Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones

ABSTRACT

Compounds of the formula   &lt;IMAGE&gt;   wherein R is halogen, C1-C4 alkoxy, C1-C4 alkyl, C1-C4 haloalkyl, cyano, nitro, (S(O)nR wherein R is C1-C4 alkyl and n is the integer 0, 1 or 2; and R2 through R8 are hydrogen or certain substituents, their salts, herbicidal compositions containing the compound or salts and the herbicidal use thereof.

CROSS-REFERENCE TO RELATED APPLICATIONS

This is a divisional of application Ser. No. 880,370, filed June 30, 1986, now U.S. Pat. No. 4,780,127.

This application is also a continuation-in-part application of Ser. No. 802,133, filed Nov. 29, 1985; which in turn is a continuation-in-part application of Ser. No. 683,898, filed Dec. 20, 1984 now abandoned.

Applicants specifically incorporate by reference the contents of the above listed U.S. patent applications.

BACKGROUND OF THE INVENTION

Compounds having the structural formula ##STR2## wherein X can be alkyl, n can be 0, 1, or 2, and R₁ can be phenyl or substituted phenyl are described in Japanese Patent Application No. 84632-1974 as being intermediates for the preparation of herbicidal compounds of the formula ##STR3## wherein R₁, X, and n are as defined above and R₂ is alkyl, alkenyl, or alkynyl. Specifically taught herbicidal compounds of this latter group are those where n is 2, X is 5,5-dimethyl, R₂ is allyl and R₁ is phenyl, 4-chlorophenyl or 4-methoxyphenyl.

The precursor intermediates for these three specifically taught compounds have no or almost no herbicidal activity.

DESCRIPTION OF THE INVENTION

Embodiment A of this invention relates to certain novel 2-(2-substituted benzoyl)-cyclohexane-1,3-diones as herbicides. The compounds of this embodiment have the following structural formula ##STR4## wherein

R and R¹ are hydrogen, C₁ -C₄ alkyl, preferably methyl or isopropyl, R^(a) OC(O)--, where R^(a) is C₁ -C₄ alkyl; most preferably R and R¹ are hydrogen;

R² is chlorine, bromine, iodine or C₁ -C₄ alkoxy, preferably methoxy; most preferably R₂ is chlorine, bromine or methoxy;

R³, R⁴ and R⁵ independently are hydrogen or an aliphatic group, preferably: (1) hydrogen; (2) halogen, preferably chlorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) --wherein R^(b) is C₁ -C₄ alkyl, preferably methyl, C₁ -C₄ haloalkyl, phenyl, benzyl, --NR^(d) R^(e) independently are hydrogen or C₁ -C₄ alkyl; and n is the integer 0, 1 or 2, preferably 2; ##STR5## wherein R^(c) is C₁ -C₄ alkyl and R^(j) is hydrogen or C₁ -C₄ alkyl, preferably methyl; (11) R^(f) C(O) wherein R^(f) is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy; (12) --NR^(g) R^(h) wherein R^(g) and R^(h) independently are hydrogen or C₁ -C₄ alkyl; or less preferably (13) R³ and R⁴ together can form a ring structure with two adjacent carbon atoms of the phenyl ring.

R³ and R⁴ can also be (14) C₃ -C₅ alkenyloxy (thio) optionally substituted, preferably with halogen or (15) C₃ -C₅ alkynyloxy (thio), optionally substituted, preferably with halogen.

Most preferably, R³ is chlorine, hydrogen, dimethylamino or methoxy. Preferably, R⁴ is hydrogen, chlorine, nitro, SO₂ CH₃, SO₂ N(CH₃)₂ or trifluoromethyl. Preferably, R⁵ is hydrogen.

Embodiment A' of this invention is an herbicidal composition comprising an herbicidally active 2-benzoyl-1,3-cyclohexanedione and an inert carrier threfor. Preferably, the 2-position of the benzoyl moiety is substituted with chlorine, bromine, iodine or C₁ -C₄ alkoxy; more preferably chlorine, bromine or methoxy; most preferably chlorine. The 5-position of the 1,3-cyclohexanedione moiety can be substituted with one or two C₁ -C₄ alkyl groups, preferably methyl, although such a substitution is not preferred.

The compounds of Embodiment A of this invention can have the following four structural formulae because of tautomerism: ##STR6## wherein R, R¹, R², R³, R⁴ and R⁵ are as defined above.

The circled proton on each of the four tautomers is reasonably labile. These protons are acidic and can be removed by any base to give a salt having an anion of the following four resonance forms: ##STR7## wherein R, R¹, R², R³, R⁴ and R⁵ are as defined above.

Examples of cations of these bases are inorganic cations such as alkali metals, e.g. lithium, sodium, and potassium, alkaline earth metals, e.g. barium, magnesium, calcium and strontium or organic cations such as substituted ammonium, sulfonium or phosphonium wherein the substituent is an aliphatic or aromatic group.

In the above description of the compounds of this invention, alkyl and alkoxy include both straight and branched configurations; for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl.

Embodiment B of this invention relates to certain novel 2-(2-substituted benzoyl)-cyclohexane-1,3-diones as herbicides. The compounds of this embodiment have the following structural formula ##STR8## wherein

R¹⁰ is C₁ -C₆ alkyl, preferably C₁ -C₄, more preferably methyl; R¹¹ is hydrogen or C₁ -C₆ alkyl, preferably C₁ -C₄, more preferably methyl or ##STR9## wherein R^(a) is C₁ -C₄ alkyl or R¹⁰ and R¹¹ together are alkylene having 3 to 6 carbon atoms, most preferably R¹¹ is hydrogen or methyl;

R¹² is chlorine, bromine, iodine, fluorine or C₁ -C₄ alkoxy, preferably methoxy; most preferably R¹² is chlorine, bromine or methoxy;

R¹³ and R¹⁴ independently are (1) hydrogen or an aliphatic group, preferably hydrogen; (2) halogen, preferably, fluorine, chlorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ aliphatic alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalykyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) --wherein R^(b) is C₁ -C₄ alkyl, preferably methyl, C₁ -C₄ haloalkyl, phenyl, benzyl, --NR^(d) R^(e) wherein R^(d) and R^(e) independently are hydrogen or C₁ -C₄ alkyl; and n is the integer 0, 1 or 2, preferably 2; ##STR10## wherein R^(c) is C₁ -C₄ alkyl and R^(j) is hydrogen or C₁ -C₄ alkyl, preferably methyl; (11) R^(f) C(O) wherein R^(f) is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy; (12) --NR^(g) R^(h) wherein R^(g) and R^(h) independently are hydrogen or C₁ -C₄ alkyl; (13) C₁ -C₄ alkylthio or less preferably (14) R¹³ and R¹⁴ together can form a ring structure with two adjacent carbon atoms of the phenyl ring to which they are attached or less preferably (15) R¹³ and R¹⁴ are the groups phenoxy or substituted phenoxy wherein the substituent is halogen or halomethyl or both;

R¹⁵, R¹⁶, R¹⁷ and R¹⁸ are independently the same or different and are selected from the group consisting of hydrogen, C₁ -C₆ alkyl, preferably C₁ -C₄ alkyl, more preferably methyl, most preferably hydrogen or methyl, and their salts;

provided, however, that R¹⁵ and R¹⁶ together may form a substituted or unsubstituted alkylene ring of 2-5 carbon atoms, the preferred substituent being 1 or 2 methyl groups.

More preferably, R¹³ is chlorine, hydrogen, methyl, alkylthio or methoxy. Preferably R¹⁴ is hydrogen, chlorine, nitro, trifluoromethyl, or R^(b) SO_(n) wherein R^(b) is C₁ -C₄ alkyl, preferably methyl and n is the integer 0, 1 or 2, preferably 2.

The compounds of Embodiment B of this invention can have the following four structural formulae because of tautomerism: ##STR11## wherein R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ and R¹⁸ are as defined above.

The circled proton on each of the four tautomers is reasonably labile. These protons are acidic and can be removed by any base to give a salt having an anion of the following four resonance forms: ##STR12## wherein R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ and R¹⁸ are as defined above.

Examples of cations of these bases are inorganic cations such as alkali metals e.g. lithium, sodium, and potassium, alkaline earth metals, e.g. barium, magnesium, calcium and strontium, or organic cations such as substituted ammonium, sulfonium or phosphonium wherein the substitutent is an aliphatic or aromatic group.

The term "aliphatic group" is used form Embodiments A and B herein in a broad sense to cover a large class of organic groups characterized by being derived from (1) and acylic (open-chain structure) of the paraffin, olefin and acetylene hydrocarbon series and their derivatives or (2) alicyclic compounds. The aliphatic group can have from 1 to 10 carbon atoms.

The term "aromatic group" is used for Embodiments A and B herein in a broad sense to distinguish from the aliphatic group and includes a group derived from (1) compounds having 6 to 20 carbon atoms and characterized by the presence of at least one benzene ring, including monocyclic, bicyclic and polycyclic hydrocarbons and their derivatives and (2) heterocyclic compounds having 5 to 19 carbon atoms which are similar in structure and are characterized by having an unsaturated ring structure containing at least one atom other than carbon such as nitrogen, sulfur and oxygen and derivatives of these heterocyclic compounds.

In the above description of the compounds of this invention alkyl and alkoxy include both straight and branched configurations; for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl.

Embodiment C of this invention relates to certain novel 2-(2-cyanobenzoyl)cyclohexane-1,3-diones as herbicides. The compounds of of this embodiment have the following structural formula ##STR13## wherein R²¹ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R²¹ is hydrogen or methyl;

R²² is hydrogen; C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl or ##STR14## wherein R^(a) is C₁ -C₄ alkyl, most preferably R²² is hydrogen or methyl; or R²¹ and R²² together are alkylene having 3 to 6 carbon atoms;

R²³ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl,more preferably methyl; most preferably R²³ is hydrogen or methyl;

R²⁴ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R²⁴ is hydrogen or methyl;

R²⁵ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R²⁵ is hydrogen or methyl;

R²⁶ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R²⁶ is hydrogen; R²⁷ and R²⁸ independently are (1) hydrogen; (2) halogen, preferably chlorine, fluorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) --wherein n is the integer 0, 1 or 2, preferably 2; and

R^(b) is

(a) C₁ -C₄ alkyl, preferably methyl;

(b) C₁ -C₄ alkyl substituted with halogen or cyano, preferably chloromethyl, trifluoromethyl or cyanomethyl;

(c) penyl; or

(d) benzyl;

(10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)--wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) --SO₂ NR^(c) R^(d) are as defined, with the proviso that R²⁷ is not attached to the 6-position.

Preferably, R²⁷ is in the 3-position. Most preferably R²⁷ is hydrogen and R²⁸ is hydrogen, chlorine, bromine, fluorine, trifluoromethyl, or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl, preferably methyl.

Salts of the above-described compounds (as defined hereinafter) are also the subject of the instant invention.

The compounds of this embodiment can have the following four structural formulae because of tautomerism: ##STR15## wherein R²¹, R²², R²³, R²⁴, R²⁵, R²⁶, R²⁷ and R²⁸ are as defined above.

The circled proton on each of the four tautomers is reasonably labile. These protons are acidic and can be removed by any base to give a salt having an anion of the following four resonance forms: ##STR16## wherein R²¹, R²², R²³, R²⁴, R²⁵, R²⁶, R²⁷ and R²⁸ are as defined above.

Examples of cations of these bases are inorgaic cations such as alkali metals e.g. lithium, sodium, and potassium organic cations such as substituted ammonium, sulfonium or phosphonium wherein the substitutent is an aliphatic or aromatic group.

Embodiment D of this invention relates to 2-(2-nitrobenzoyl)-1,3-cyclohexanediones and their use as herbicides.

The compounds have a nitro substitution in the 2-position of the phenyl moiety of their compounds. The nitro substitution imparts exceptional herbicidal acitivity to the compounds of this invention.

Embodiment D' of this invention is an herbicidal composition comprising an herbicidally active 2-(2-nitrobenzoyl)-1,3-cyclohexanedione and an inert carrier therefor. The 4-, 5- and 6-positions of the 1,3-cyclohexanedione moiety can be substituted, preferably with the groups hereinafter recited. More preferably, the 1,3-cyclohexanedione moiety has no substitution or the 4- or 6-positions are substituted with one or two methyl groups. The 3-, 4- and 5-positions of the benzoyl moiety can be substituted, preferably with the groups hereinafter recited.

The novel compounds of Embodiment D have the following structural formula ##STR17## wherein

R³¹ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R³¹ is hydrogen or methyl;

R³² is hydrogen; C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl or ##STR18## wherein R^(a) is C₁ -C₄ alkyl, most preferably R³² is hydrogen or methyl; or

R³¹ and R³² together are alkylene having 3 to 6 carbon atoms;

R³³ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R³³ is hydrogen or methyl;

R³⁴ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R³⁴ is hydrogen or methyl;

R³⁵ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R³⁵ is hydrogen or methyl;

R³⁶ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R³⁶ is hydrogen;

R³⁷ and R³⁸ independently are (1) hydrogen; (2) halogen, preferably chlorine, fluorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) --wherein n is the integer 0, 1 or 2, preferably 2; and

R^(b) is

(a) C₁ -C₄ alkyl, preferably methyl;

(b) C₁ -C₄ alkyl substituted with halogen or cyano, preferably chloromethyl, trifluoromethyl or cyanomethyl;

(c) phenyl; or

(d) benzyl;

(10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)--wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) --SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined, with the proviso that R³⁷ is not attached to the 6-position.

Preferably, R³⁷ is in the 3-position. Most preferably R³⁷ is hydrogen or C₁ -C₄ alkoxy and R³⁸ is hydrogen, chlorine, bromine, fluorine, trifluoromethyl, or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl, preferably methyl.

The term "C₁ -C₄ alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and t-butyl. The term "halogen" includes chlorine, bromine, iodine and fluorine. Ther terms "C₁ -C₄ alkoxy" includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and t-butoxy. The term "haloalkyl" includes the eight alkyl groups with one or more hydrogens replaced by chlorine, bromine, iodine or fluorine.

Salts of the above-described compounds (as defined hereinafter) are also the subject of the instant invention.

The compounds of this invention can have the following four structural formulae because of tautomerism: ##STR19## wherein R³¹, R³², R³³, R³⁴, R³⁵, R³⁶, R³⁷ and R³⁸ are as defined above.

The circled proton on each of the four tautomers is reasonably labile. These protons are acidic and can be removed by any base to give a salt having an anion of the following four resonance forms: ##STR20## wherein R³¹, R³², R³³, R³⁴, R³⁵, R³⁶, R³⁷ and R³⁸ are as defined above.

Examples of cations of these bases are inorganic cations such as alkali metals e.g. lithium, sodium, and potassium or organic cations such as substituted ammonium, sulfonium or phosphonium wherein the substitutent is an aliphatic or aromatic group.

Embodiment E of this invention relates to 2-(2-benzoyl)-1,3-cyclohexanediones and their use as herbicides.

Embodiment E' of this invention is an herbicidal composition comprising an herbicidally active 2-(2-C₁ -C₄ alkylthio, C₁ -C₄ alkylsulfinyl or C₁ -C₄ alkylsulfonyl benzoyl)-1,3-cyclohexanedione and an inert carrier therefor. The 4-, 5- and 6-positions of the 1,3-cyclohexanedione moiety can be substituted, preferably with the groups hereinafter recited. More preferably, the 1,3-cyclohexanedione moiety has no substitution or the 4- or 6-positions are substituted with one or two methyl groups. The 3-, 4- and 5-positions of the benzoyl moiety can be substituted, preferably with the groups hereinafter recited.

The novel compounds of Embodiment E have the structural formula ##STR21## wherein

n is the integer 0, 1 or 2, preferably 2;

R⁴⁰ is C₁ -C₄ alkyl, preferably methyl;

R⁴¹ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R⁴¹ is hydrogen or methyl;

R⁴² is hydrogen; C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl or ##STR22## wherein R^(a) is C₁ -C₄ alkyl, most preferably R⁴² is hydrogen or methyl; or R⁴¹ and R⁴² together are alkylene having 3 to 6 carbon atoms;

R⁴³ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R⁴³ is hydrogen or methyl;

R⁴⁴ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R⁴⁴ is hydrogen or methyl;

R⁴⁵ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R⁴⁵ is hydrogen or methyl;

R⁴⁶ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R⁴⁶ is hydrogen;

R⁴⁷ and R⁴⁸ independently are (1) hydrogen; (2) halogen, preferably chlorine, fluorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) --wherein n is the integer 0, 1 or 2, preferably 2; and

R^(b) is

(a) C₁ -C₄ alkyl, preferably methyl;

(b) C₁ -C₄ alkyl substituted with halogen or cyano, preferably chloromethyl, trifluoromethyl or cyanomethyl;

(c) phenyl; or

(d) benzyl;

(10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) --SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined, with the proviso that R⁴⁷ is not attached to the 6-position.

Preferably, R⁴⁷ is in the 3-position. Most preferably R⁴⁷ is hydrogen or 3-chlorine and R⁴⁸ is hydrogen, chlorine, bromine, fluorine, trifluoromethyl, or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl, preferably methyl.

The term "C₁ -C₄ " alkyl includes methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and t-butyl. The term "halogen" includes chlorine, bromine, iodine and fluorine. The term "C₁ -C₄ alkoxy" includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and t-butoxy. The term "haloalkyl" includes the eight alkyl groups with one or more hydrogens replaced by chloro, bromo, iodo or fluoro.

Salts of the above-described compounds (as defined hereinafter) are also the subject of the instant invention.

The compounds of this invention can have the following four structural formulae because of tautomerism: ##STR23## wherein n, R⁴⁰, R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵, R⁴⁶, R⁴⁷ and R⁴⁸ are as defined above.

The circled proton on each of the four tautomers is reasonably labile. These protons are acidic and can be removed by any base to give a salt having an anion of the following four resonance forms: ##STR24## wherein n, R⁴⁰, R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵, R⁴⁶, R⁴⁷ and R⁴⁸ are as defined above.

Examples of cations of these bases are inorganic cations such as alkali metals e.g. lithium, sodium, and potassium, organic cations such as substituted ammonium, sulfonium or phosphonium wherein the substitutent is an aliphatic or aromatic group.

Embodiment F of this invention relates to 2-(2-alkylbenzoyl)-1,3-cyclohexanediones and their use as herbicides.

Embodiment F' of this invention is an herbicidal composition comprising an herbicidally active 2-benzoyl-1,3-cyclohexanedione and an inert carrier therefor wherein the 2-position of the benzoyl moiety is substituted with C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, optionally substituted with halogen, more preferably methyl or trifluoromethyl and the 4-position preferably is substituted with an electron withdrawing group, such as halogen, cyano, trifluoromethyl or nitro. The 4-, 5- and 6positions of the 1,3-cyclohexanedione moiety can be substituted, preferably with the groups hereinafter recited. More preferably, the 1,3-cyclohexanedione moiety has no substitution or the 4- or 6-positions are substituted with one or two methyl groups. The 3-, 4- and 5-positions of the benzoyl moiety can be substituted, preferably with the groups hereinafter recited.

The novel compounds of Embodiment F have the following structural formula ##STR25## wherein

R⁵⁰ is C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, optionally substituted with halogen, more preferably methyl and trifluoromethyl;

R⁵¹ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R⁵¹ is hydrogen or methyl;

R⁵² is hydrogen; C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl or ##STR26## wherein R^(a) is C₁ -C₄ alkyl, most preferably R⁵² is hydrogen or methyl; or R⁵¹ and R⁵² together are alkylene having 3 to 6 carbon atoms;

R⁵³ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R⁵³ is hydrogen or methyl;

R⁵⁴ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R⁵⁴ is hydrogen or methyl;

R⁵⁵ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R⁵⁵ is hydrogen or methyl;

R⁵⁶ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R⁵⁶ is hydrogen;

R⁵⁷ and R⁵⁸ independently are (1) hydrogen; (2) halogen, preferably chlorine, fluorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethy; (9) R^(b) SO_(n) --wherein n is the integer 0, 1 or 2, preferably 2; and

R^(b) is

(a) C₁ -C₄ alkyl, preferably methyl;

(b) C₁ -C₄ alkyl substituted with halogen or cyano, preferably chloromethyl, trifluoromethyl or cyanomethyl;

(c) phenyl; or

(d) benzyl;

(10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)--wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) --SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined, with the proviso that R⁵⁷ is not attached to the 6-position.

The term "C₁ -C₄ alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, sec-butyl, isobutyl and t-butyl. The term "halogen" includes chlorine, bromine, iodine and fluorine. The term "C₁ -C₄ alkoxy" includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and t-butoxy. The term "haloalkyl" includes the eight alkyl groups with one or more hydrogens replaced by chloro, bromo, iodo or fluoro.

Preferably, R⁵⁷ is in the 3-position. Most preferably R⁵⁷ is hydrogen and R⁵⁸ is hydrogen, chlorine, bromine, fluorine, trifluoromethyl, or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl, preferably methyl.

Salts of the above-described compounds (as defined hereinafter) are also the subject of the instant invention.

The compounds of this invention can have the following four structural formulae because of tautomerism: ##STR27## wherein R⁵⁰, R⁵¹, R⁵², R⁵³, R⁵⁴, R⁵⁵, R⁵⁶, R⁵⁷ and R⁵⁸ are as defined above.

The circled proton on each of the four tautomers is reasonably labile. These protons are acidic and can be removed by any base to give a salt having an anion of the following four resonance forms: ##STR28## wherein R⁵⁰, R⁵¹, R⁵², R⁵³, R⁵⁴, R⁵⁵, R⁵⁶, R⁵⁷ and R⁵⁸ are as defined above.

Examples of cations of these bases are inorganic cations such as alkali metals e.g. lithium, sodium, and potassium organic cations such as substituted ammonium, sulfonium or phosphonium wherein the substituent is an aliphatic or aromatic group.

Embodiment G of this invention relates to 2-benzoyl-1,35-cyclohexanetriones and their use as herbicides.

Embodiment G' of this invention is an herbicical composition comprising an herbicidally active 2-benzoyl-substituted-1,3,5-cyclohexanetrione and an inert carrier therefor. The 4- and 6-positions of the 1,35-cyclohexanetrione moiety are preferably substituted with groups hereinafter defined, most preferably with all methyl groups. The benzoyl moiety can be substituted, preferably with the groups hereinafter recited.

The novel compounds of Embodiment G have the following structural formula ##STR29## wherein R⁶⁰ is hydrogen; halogen; C₁ -C₂ alkyl, preferably methyl; C₁ -C₂ alkoxy, preferably methoxy; nitro; cyano; C₁ -C₂ haloalkyl, preferably trifluoromethyl; R^(a) SO_(n) --wherein n is 0 or 2, preferably 2 and R^(a) is C₁ -C₂ alkyl, preferably methyl, trifluoromethyl or difluoromethyl; or trifluoromethoxy or difluoromethoxy. Preferably, R⁶⁰ is chlorine, bromine, C₁ -C₂ alkyl, C₁ -C₂ alkoxy, trifluoromethyl, cyano, nitro, C₁ -C₂ alkylthio or C₁ -C₂ alkylsulfonyl; more preferably chlorine, nitro, methyl, trifluoromethyl or methylsulfonyl; and

R⁶¹ is hydrogen or C₁ -C₄ alkyl, preferably methyl;

R⁶² is hydrogen or C₁ -C₄ alkyl, preferably methyl; or

R⁶¹ and R⁶² together are C₂ -C₅ alkylene;

R⁶³ is C₁ -C₄ alkyl, preferably methyl;

R⁶⁴ is C₁ -C₄ alkyl, preferably methyl; or

R⁶³ and R⁶⁴ together are C₂ -C₅ alkylene;

R⁶⁵ and R⁶⁶ independently are (1) hydrogen; (2) halogen, preferably chlorine, fluorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) --wherein n is the integer 0, 1 or 2, preferably 2; and

R^(b) is

(a) C₁ -C₄ alkyl, preferably methyl;

(b) C₁ -C₄ alkyl substituted with halogen or cyano, preferably chloromethyl, trifluoromethyl or cyanomethyl;

(c) phenyl; or

(d) benzyl;

(10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)--wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; (12) --SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined; or (13) --N(R^(c))C(O)R^(d) wherein R^(c) and R^(d) are as defined.

Preferably R⁶⁵ is in the 3-position. More preferably R⁶⁵ is hydrogen, chlorine, fluorine, trifluoromethyl, cyano, C₁ -C₄ alkoxy or C₁ -C₄ thioalkyl. Most preferably, R⁶⁵ is hydrogen. Preferably R⁶⁶ is in the 4-position. Most preferably R⁶⁶ is halogen, cyano, trifluoromethyl, or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl, preferably methyl or C₁ -C₄ haloalkyl, preferably chloromethyl, difluoromethyl or trifluoromethyl.

The term "C₁ -C₄ alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and t-butyl. The term "halogen" includes chlorine, bromine, iodine and fluorine. The terms "C₁ -C₄ alkoxy" includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and t-butoxy. The term "C₁ -C₄ haloalkyl" includes the alkyl groups defined above under C₁ -C₄ alkyl in which one or more hydrogens is replaced by chlorine, bromine, iodine or fluorine.

Salts of the above-described compounds (as defined hereinafter) are included within the scope of the instant invention.

The compounds of this invention can have the following four structural formulae because of tautomerism: ##STR30## wherein R⁶⁰, R⁶¹, R⁶², R⁶³, R⁶⁴, R⁶⁵ and R⁶⁶ are as defined above.

The circled proton on each of the four tautomers is reasonably labile. These protons are acidic and can be removed by reaction with a base to form a salt having an anion of the following four resonance forms: ##STR31## wherein R⁶⁰, R⁶¹, R⁶², R⁶³, R⁶⁴, R⁶⁵ and R⁶⁶ are as defined above.

Examples of cations of these bases are inorganic cations such as alkalimetals, e.g., lithium, sodium and potassium; the alkaline earth metals, e.g. calcium and magnesium or ammonium or organic cations such as substituted ammonium, sulfonium, sulfoxonium or phosphonium wherein the substituents are aliphatic or aromatic groups.

Those skilled in the art will recognize in considering the salts of this invention that varying degrees os association between the anion and cation will exist depending upon the nature of the cation. In some instances with a suitable cation, such as copper, the salt can exist in a chelated form.

The compounds of this invention and their salts are active herbicides of a general type. That is, they are herbicidally effective against a wide range of plant species. The method of controlling undesirable vegetation of the present invention comprises applying an herbicidally effective amount of the above-described compounds to the area where control is desired.

The compounds of Embodiments A and A' of the present invention can be prepared by the following general method. ##STR32##

Generally, mole amounts of the dione and substituted benzoyl cyanide are used, along with a slight mole excess of zinc chloride. The two reactants and the zinc chloride are combined in a solvent such as methylene chloride. A slight mole excess of triethylamine is slowly added to the reaction mixture with cooling. The mixture is stirred at room temperature for 5 hours.

The reaction product is worked up by conventional techniques.

The above-described substituted benzoyl cyanide can be prepared according to the teaching of T. S. Oakwood and C. A. Weisgerber, Organic Synthesis Collected, Vol. III, pp. 122 (1955).

The following example teaches the synthesis of a representative compound of Embodiments A and A' of this invention.

EXAMPLE 1-A,A' 2-(2,4-Dichlorobenzoyl)-cyclohexane-1,3-dione ##STR33##

1,3-Cyclohexanedione [11.2 grams (g), 0.1 mole], 20.0 g (0.1 mole) 2,3-dichlorobenzoyl cyanide and 13.6 g (0.11 mole) anhydrous, powdered zinc chloride were combined in 100 milliliters (ml) methylene chloride. Triethylamine (10.1 g, 0.12 mole) was slowly added with cooling. The reaction mixture was stirred at room temperature for 5 hours and then poured into 2N hydrochloric acid. The aqueous phase was discarded and the organic phase was washed with 150 ml 5% Na₂ CO₃ four times. The aqueous washings were combined and acidified with HCl, extracted with methylene chloride, dried and concentrated to yield 25.3 g of crude product. The crude product was dissolved in ether and stirred with 250 ml of 5% copper (II) acetate. The resulting copper salt was filtered, washed with ether and stirred with 6N hydrochloric acid to destroy the salt. The extract was washed with ether to yield 22.15 grams of the desired product m.p. 138°-140° C. (77.7% yield). The structure was confirmed by instrumental analysis.

The compounds of Embodiment B of the present invention can be prepared by the following general method. ##STR34##

Generally, mole amounts of the dione and substituted benzoyl cyanide are used, along with a slight mole excess of zinc chloride. The two reactants and the zinc chloride are combined in a solvent such as methylene chloride. A slight mole excess of triethylamine is slowly added to the reaction mixture with cooling. The mixture is stirred at room temperature for 5 hours.

The reaction product is worked up by conventional techniques.

The above-described substituted benzoyl cyanide can be prepared according to the teaching of T. S. Oakwood and C. A. Weisgerber, Organic Synthesis Collected, Vol. III, pp. 122 (1955).

The following example teaches the synthesis of representative compound of Embodiment B of this invention.

EXAMPLE 1-B 4,4-Dimethyl-2-(2,4-dichlorobenzoyl)-cyclohexane-1,3-dione ##STR35##

4,4-Dimethyl-1,3-cyclohexanedione [14.0 grams (g), 0.1 mole], 20.0 g (0.1 mole) 2,4-dichlorobenzoyl cyanide and 13.6 (0.11 mole) anhydrous, powdered zinc chloride were combined in 100 milliliters (ml) methylene chloride. Triethylamine (10.1 g, 0.12 mole) was slowly added with cooling. The reaction mixture was stirred at room temperature for 5 hours and then poured into 2N hydrochloric acid. The aqueous phase was discarded and the organic phase was washed with 150 ml 5% Na₂ CO₃ four times. The aqueous washings were combined and acidified with HCl, extracted with methylene chloride, dried and concentrated to yield 25.3 g of crude product. The crude product was chromatographed (2% AcOH/CH₂ Cl₂) in 5 g aliquots then reduced on rotavap under reduced pressure at 50° C. for 30 minutes to remove AcOH. This yielded an oil (40% yield). The structure was confirmed by instrumental analysis.

The compounds of Embodiment C of the present invention can be prepared by the following general method. ##STR36##

Generally, in step (1) mole amounts of the dione and substituted benzoyl chloride are used, along with a slight mole excess of triethylamine. The two reactants are combined in a solvent such as methylene chloride. The triethylamine is slowly added to the reaction mixture with cooling. The mixture is stirred at room temperature for several hours.

The reaction product is worked up by conventional techniques. ##STR37##

Generally, in step (2) a mole of the enol ester intermediate is reacted with 1 to 4 moles of the triethylamine, preferably 2 moles of the triethylamine and up to 0.5 mole, preferably 0.1 mole of a cyanide source (e.g., potassium cyanide or acetone cyanohydrin). The mixture is stirred in a reaction pot for about one hour at room temperature and the desired product is recovered by conventional techniques.

The above described substituted benzoyl chlorides can be prepared from the corresponding substituted benzoic acids according to the teaching of Reagents for Organic Synthesis, Vol. I, L. F. Fieser and M. Fieser, pp. 767-769 (1967). ##STR38## wherein R²⁷ and R²⁸ are as previously defined.

The substituted benzoic acids can be prepared by a wide variety of general methods according to the teaching of The Chemistry of Carboxylic Acids and Esters, S. Patai, editor, J. Wiley and Sons, New York, N.Y. (1969) and Survey of Organic Synthesis, C. A. Buehler and D. F. Pearson, J. Wiley and Sons, (1970).

The following are two representative examples of the methods described therein. ##STR39## wherein R²⁷ and R∞are as previously defined.

In reaction (a) the substituted acetophenone is heated to reflux for several hours in an aqueous hypochlorite solution. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR40## wherein R²⁷ and R²⁸ are as previously defined.

In reaction (b) the substituted toluene is heated to reflux in an aqueous solution of potassium permanganate for several hours. The solution is then filtered and the reaction product is isolated by conventional techniques.

The following example teaches the synthesis of a representative compound of Embodiment C of this invention.

EXAMPLE 1-C 2-(2'-Cyanobenzoyl)-4,4-dimethyl-1,3-cyclohexanedione ##STR41##

2-Cyanobenzoyl chloride (3.9 g, 24 mmol) and 4,4-dimethyl-1,3-cyclohexanedione (3.3g, 24 mmol) were dissolved in 75 ml methylene chloride. Triethylamine (5.0 ml, 36 mmol) was added dropwise and the resulting solution stirred for one and one-half hours at room temperature. The solution was washed with water, 2 normal hydrochloric acid (2N HCl), 5% potassium carbonate solution (5% K₂ CO₃) and saturated sodium chloride solution (brine), dried over anhydrous magnesium sulfate (MgSO₄) and concentrated under vacuum. The residue was dissolved in 20 ml acetonitrile. Triethylamine (4.4 ml, 32 mmol) and acetone cyanohydrin (5 drops) were added and the solution stirred for two hours. After dilution with ether, the solution was washed with 2N HCl and extracted with 5% K₂ CO₃. The aqueous extract was acidified with concentrated hydrochloric acid and extracted with ether. The ether was washed with water and brine, dried (MgSO₄) and concentrated under vacuum. The residue was purified by silica gel chromatography, yielding 1.2 g of a viscous oil which was identified as the desired compound by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy.

The compounds of Embodiments D and D' of the present invention can be prepared by the following two-step general method.

The process proceeds via the production of an enol ester intermediate as shown in reaction (1). The final product is obtained by rearrangement of the enol ester as shown in reaction (2). The two reactions may be conducted as separate steps by isolation and recovery of the enol ester using conventional techniques prior to conducting step (2), or by addition of a cyanide source to the reaction medium after the formation of the enol ester, or in one step by inclusion of the cyanide source at the start of reaction (1). ##STR42## wherein R³¹ through R³⁸ and moderate base are as defined and X is halogen, preferably chlorine, C₁ -C₄ alkyl-C(O)--O--, C₁ -C₄ alkoxy-C(O)--O--or ##STR43## wherein R³⁷ and R³⁸ in this portion of the molecule are identical with those in the reactant shown above and the moderate base is as defined, preferably tri-C₁ -C₆ alkylamine, alkali metal carbonate or alkali metal phosphate.

Generally, in step (1) mole amounts of the dione and substituted benzoyl reactant are used, along with a mole amount or excess of the base. The two reactants are combined in an organic solvent such as methylene chloride, toluene, ethyl acetate or dimethylformamide. The base or benzoyl reactant preferably are added to the reaction mixture with cooling. The mixture is stirred at 0° C. -50° C. until the reaction is substantially complete. ##STR44## wherein the moderate base and R³¹ through R³⁸ are as defined above.

Generally, in step (2) a mole of the enol ester intermediate is reacted with 1 to 4 moles of the base, preferably about 2 moles of moderate base and from 0.01 mole to about 0.5 mole or higher, preferably around 0.1 mole of the cyanide source (e.g., potassium cyanide or acetone cyanohydrin). The mixture is stirred in a reaction pot until the rearrangement is substantially complete at a temperature below 50° C., preferably about 20° C. to about 40° C., and the desired product is recovered by conventional techniques.

The term "cyanide source" refers to a substance or substances which under the rearrangement conditions consists of or generates hydrogen cyanide and/or cyanide anion.

The process is conducted in the presence of a catalytic amount of a source of cyanide anion and/or hydrogen cyanide, together with a molar excess, with respect to the enol ester, of a moderate base.

Preferred cyanide sources are alkali metal cyanides such as sodium and potassium cyanide; cyanohydrins of methyl alkyl ketones having from 1-4 carbon atoms in the alkyl groups, such as acetone or methyl isobutyl ketone cyanohydrins; cyanohydrins of benzaldehyde or of C₂ -C₅ aliphatic aldehydes such as acetaldehyde, propionaldehyde, etc., cyanohydrins; zinc cyanide; tri(lower alkyl) silyl cyanides, notably trimethyl silyl cyanide; and hydrogen cyanide itself. Hydrogen cyanide is considered most advantageous as it produces relatively rapid reaction and is inexpensive. Among cyanohydrins the preferred cyanide source is acetone cyanohydrin.

The cyanide source is used in an amount up to about 50 mole percent based on the enol ester. It may be used in as little as about 1 mole percent to produce an acceptable rate of reaction at about 40° C. on a small scale. Larger scale reactions give more reproducible results with slightly higher catalyst levels of about 2 mole percent. Generally about 1-10 mole % of the cyanide source is preferred.

The process is conducted with a molar excess, with respect to the enol ester, of a moderate base, By the term "moderate base" is meant a substance which acts as a base yet whose stength or activity as a base lies between that of strong bases such as hydroxides (which could cause hydrolysis of the enol ester) and that of weak bases such as bicarbonates (which would not function effectively). Moderate bases suitable for use in this embodiment include both organic bases such as tertiary amines and inorganic bases such as alkali metal carbonates and phosphates. Suitable tertiary amines include trialkylamines such as triethylamine. Suitable inorganic bases include potassium carbonate and trisodium phosphate.

The base is used in an amount of from about 1 to about 4 moles per mole of enol ester, preferably about 2 moles per mole.

When the cyanide source is an alkali metal cyanide, particularly potassium cyanide, a phase transfer catalyst may be included in the reaction. Particularly suitable phase transfer catalysts are the Crown ethers.

A number of different solvents may be usable in this process, depending on the nature of the acid chloride or the acylated product. A preferred solvent for this reaction is 1,2-dichloroethane. Other solvents which may be employed, depending on the reactants or products include toluene, acetonitrile, methylene chloride, ethyl acetate, dimethylformamide, and methyl isobutyl ketone (MIBK).

In general, depending on the nature of the reactants and the cyanide source, the rearrangment may be conducted at temperatures up to about 50° C.

The above described substituted benzoyl chlorides can be prepared from the corresponding substituted benzoic acids according to the teaching of Reagents for Organic Synthesis, Vol. I, L. F. Fieser and M. Fieser, pp. 767-769 (1967). ##STR45## wherein R³⁷ and R³⁸ are as previously defined.

The substituted benzoic acids can be prepared by a wide variety of general methods according to the teaching of The Chemistry of Carboxylic Acids and Esters, S. Patai, editor, J. Wiley and Sons, New York, N.Y. (1969) and Survey of Organic Synthesis, C. A. Buehler and D. F. Pearson, J. Wiley and Sons, (1970).

The following are three representative examples of the methods described therein. ##STR46## wherein R³⁷ and R³⁸ are as previously defined.

In reaction (a) the substituted benzonitrile is heated to reflux in aqueous sulfuric acid for several hours. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR47## wherein R³⁷ and R³⁸ are as previously defined.

In reaction (b) the substituted acetophenone is heated to reflux for several hours in an aqueous hypochlorite solution. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR48## wherein R³⁷ and R³⁸ are as previously defined.

In reaction (c) the substituted toluene is heated to reflux in an aqueous solution of potassium permanganate for several hours. The solution is then filtered and the reaction product is isolated by conventional techniques.

The following examples teach the synthesis of representative compounds of Embodiment D and D' of this invention.

EXAMPLE 1-D,D' 2-(2'-Nitrobenzoyl)-1,3-cyclohexanedione ##STR49##

2-Nitrobenzoyl chloride (5.0 g, 27 mmol) and cyclohexanedione (3.0 g, 27 mmol) were dissolved in methylene chloride. Triethylamine (4.9 ml, 35 mmol) was added dropwise and the resulting solution stirred for one hour. The solution was washed with 2 normal hydrochloric acid (2N HCl), water, 5% potassium carbonate solution and saturated sodium chloride solution, dried over anhydrous magnesium sulfate (MgSO₄) and concentrated under vacuum. The residue was dissolved in 20 ml acetonitrile. Triethylamine (1 equivalent) and potassium cyanide (40 mol %) were added and the solution stirred for one hour at room temperature. After dilution with ether, the solution was washed with 2N HCl and extracted with 5% potassium carbonate solution. The aqueous extract was acidified and ether was added. Filtration of the resulting mixture yielded 3.2 g of the desired compound (m.p. 132°-135° C.) which was identified by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy.

EXAMPLE 2-D,D' 2-(2'-Nitrobenzoyl)-5,5-dimethyl-1,3-cyclohexanedione ##STR50##

Triethylamine (3.4 ml, 25 mmol) was added dropwise to a methylene chloride solution of 2-nitrobenzoyl chloride (3.5 g, 19 mmol) and 5,5-dimethylcyclohexanedione (2.4 g, 19 mmol). After stirring for one hour at room temperature an additional 3 equivalents of triethylamine and 0.4 ml acetone cyanohydrin were added. The solution was stirred for 2.5 hours, then washed with 2N HCl and extracted with 5% potassium carbonate solution. The basic extracts were acidified with 2N HCl and extracted with ether. The ether portion was washed wiht saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under vacuum. The residue was recrytallized from ethyl acetate yielding 2.0 g of the desired compound (m.p. 130°-133° C.) which was identified as such by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy.

The compounds of Embodiments E and E' of the present invention can be prepared by the following two or three step general method.

The process proceeds via the production of an enol ester intermediate as shown in reaction (1). The final product is obtained by rearrangement of the enol ester as shown in reaction (2). The two reactions may be conducted as separate steps by isolation and recovery of the enol ester using conventional techniques prior to conducting step (2), or by addition of a cyanide source to the reaction medium after the formation of the enol ester, or in one step by inclusion of the cyanide source at the start of reaction (1). ##STR51## wherein moderate base, and R⁴⁰ through R⁴⁸ are defined herein, and X is halogen, preferably chlorine, C₁ -C₄ alkyl-C(O)--O--, C₁ -C₄ alkoxy-C(O)--O--or ##STR52## wherein R⁴⁰, R⁴⁷ and R⁴⁸ in this portion of the moledule are identical with those in the reactant shown above, and the moderate base is as defined, preferably tri-C₆ -C₆ alkylamine, alkali metal carbonate or alkali metal phosphate.

Generally, in step (1) mole amounts of the dione and substituted benzoyl reactant are used, along with a mole amount or excess of the base. The two reactants are combined in an organic solvent such as methylene chloride, toluene, ethyl acetate or dimethylformamide. The base or benzoyl reactant preferably are added to the reaction mixture with cooling. The mixture is stirred at 0° C.-50° C. until the reaction is substantially complete. ##STR53##

Generally, in step (2) a mole of the enol ester intermediate is reacted with 1 to 4 moles of the base, preferably about 2 moles of moderate base and from 0.01 mole to about 0.5 mole or higher, preferably around 0.1 mole of the cyanide source (e.g., potassium cyanide or acetonecyanohydrin). The mixture is stirred in a reaction pot until the rearrangement is substantially complete at a temperature below 50° C., preferably about 20° C. to about 40° C., and the desired product is recovered by conventional techniques.

The term "cyanide source" refers to a substance or substances which under the rearrangement conditions consists of or generates hydrogen cyanide and/or cyanide anion.

The process is conducted in the presence of a catalytic amount of a source of cyanide anion and/or hydrogen cyanide, together with a molar excess, with respect to the enol ester, of a moderate base.

Preferred cyanide sources are alkali metal cyanides such as sodium and potassium cyanide; cyanohydrins of methyl alkyl ketones having from 1-4 carbon atoms in the alkyl groups, such as acetone or methyl isobutyl ketone cyanohydrins; cyanohydrins of benzaldehyde or of C₂ -C₅ aliphatic aldehydes such as acetaldehyde, propionaldehyde, etc., cyanohydrins; zinc cyanide; tri(lower alkyl) silyl cyanides, notably trimethyl silyl cyanide; and hydrogen cyanide itself. Hydrogen cyanide is considered most advantageous as it produces relatively rapid reaction and is inexpensive. Among cyanohydrins the preferred cyanide source is acetone cyanohydrin.

The cyanide source is used in an amount up to about 50 mole percent based on the enol ester. It may be used in as little as about 1 mole percent to produce an acceptable rate of reaction at about 40° C. on a small scale. Larger scale reactions give more reproducible results with slightly higher catalyst levels of about 2 mole percent. Generally about 1-10 mole % of the cyanide source is preferred.

The process is conducted with a molar excess, with respect to the enol ester, of a moderate base. By the term "moderate base" is meant a substance which acts as a base yet whose strength or activity as a base lies between that of strong bases such as hydroxides (which could cause hydrolysis of the enol ester) and that of weak bases such as bicarbonates (which would not function effectively). Moderate bases suitable for use in this embodiment include both organic bases such as tertiary amines and inorganic bases such as alkali metal carbonates and phosphates. Suitable tertiary amines include trialkylamines such as triethylamine. Suitable inorganic bases include potassium carbonate and trisodium phosphate.

The base is used in an amount of from about 1 to about 4 moles per mole of enol ester, preferably about 2 moles per mole.

When the cyanide source is an alkali metal cyanide, particularly potassium cyanide, a phase transfer catalyst may be included in the reaction. Particularly suitable phase transfer catalysts are the Crown ethers.

A number of different solvents may be usable in this process, depending on the nature of the acid chloride or the acylated product. A preferred solvent for this reaction is 1,2-dichloroethane. Other solvents which may be employed, depending on the reactants or products include toluene, acetonitrile, methylene chloride, ethyl acetate, dimethylformamide, and methyl isobutyl ketone (MIBK).

In general, depending on the nature of the reactants and the cyanide source, the rearrangment may be conducted at temperatures up to about 50° C. ##STR54## wherein n is 1 or 2.

Generally in step (3), a mole of the reaction product of step (2) is reacted with a slight mole or two mole excess of of an oxidizing agent such as m-chloroperbenzoic acid after being dissolved in a solvent such as methylene chloride. After completion of the reaction, the resulting mixture is stripped under vacuum. The residue is purified by silica gel chromatography to yield the desired product.

The above described substituted benzoyl chlorides can be prepared from the corresponding substituted benzoic acids according to the teaching of Reagents for Organic Synthesis, Vol. I, L. F. Fieser and M. Fieser, pp. 767-769 (1967). ##STR55## wherein R⁴⁰, R⁴⁷ and R⁴⁸ are as previously defined.

The substituted benzoic acids can be prepared by a wide variety of general methods according to the teaching of The Chemistry of Carboxylic Acids and Esters, S. Patai, editor, J. Wiley and Sons, New York, N.Y. (1969) and Survey of Organic Synthesis, C. A. Buehler and D. F. Pearson, J. Wiley and Sons, (1970).

The following are three representative examples of the methods described therein. ##STR56## wherein R⁴⁰, R⁴⁷ and R⁴⁸ are as previously defined.

In reaction (a) the substituted benzonitrile is heated to reflux in aqueous sulfuric acid for several hours. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR57## wherein R⁴⁰, R⁴⁷ and R⁴⁸ are as previously defined.

In reaction (b) the substituted acetophenone is heated to reflux for several hours in an aqueous hypochlorite solution. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR58## wherein R⁴⁰, R⁴⁷ and R⁴⁸ are as defined and X is chlorine, bromine or iodine.

In reaction (c) the substituted aromatic halide is allowed to react with magnesium in a solvent such as ether. The solution is then poured over crushed dry ice and the benzoic acid is isolated by conventional techniques.

The following examples teach the synthesis representative compounds of Embodiments E and E' of this invention.

EXAMPLE 1-E,E' 2-(2'-Methylthiobenzoyl)-4,4,6-trimethyl-1,3-cyclohexanedione ##STR59##

2-Methylthiobenzoyl chloride (7.2 g, 39 mmol) and 4,46-trimethylcyclohexanedione (5.0 g, 39 mmol) were dissolved in methylene chloride. Triethylamine (7.0 ml, 50 mmol) was added dropwise and the resulting solution stirred for one hour at room termperature. The solution was washed with 2 normal hydrochloric acid (2N HCl), 5% potassium carbonate solution (5% K₂ CO₃) and saturated sodium chloride solution (brine), dried over anhydrous magnesium sulfate (MgSO₄) and concentrated under vacuum. The residue was dissolved in 20 ml acetonitrile. Triethylamine (2.5 equivalents) and acetone cyanohydrin (0.4 ml) were added and the solution stirred for 45 minutes at room temperature. After dilution with ether, the solution was washed with 2N HCl and extracted with 5% K₂ CO₃. The aqueous extract was acidified with hydrochloric acid and extracted with ether. The ether was washed with brine, dried (MgSO₄) and concentrated under vacuum. The residue was purified by trituration with ether, yielding 50 g of a viscous oil which was identified as the desired compound by nuclear magnetic resonance spectroscopy (nmr), infrared spectroscopy (ir) and mass spectroscopy (ms).

EXAMPLE 2-E,E' 2-(2'-Methanesulfonylbenzoyl)-4,4,6-trimethyl-1,3-cyclohexanedione ##STR60##

The benzoyl cyclohexanedione prepared in Example 1 (2.5 g, 7.9 mmol) was dissolved in 40 ml methylene chloride. m-Chloroperbenzoic acid (3.5 g, 16 mmol) was added and the resulting solution was stirred for 45 minutes. The solution was concentrated under vacuum. Purification of the residue by silica gel chromatography yielded 1.7 g of a viscous oil which was identified as the desired compound by nmr, ir and ms.

EXAMPLE 3-E,E' 2-(4'-Trifluoromethyl-2'-methanesulfinylbenzoyl-4,4-dimethyl-1,3-cyclohexanedione ##STR61##

2-(4'-Trifluoromethyl-2'-methylthiobenzoyl)-4,4-dimethyl-1,3-cyclohexanedione (5.0 g, 14 mmol) (which was prepared according to the method of Example 1) was dissolved in 50 ml methylene chloride. A solution of m-chloroperbenzoic acid (2.4 g--80%, 14 mmol) in 50 ml methylene chloride was added dropwise and the resulting solution was stirred for three hours at room temperature. After concentration under vacuum, the residue was dissolved in ether and washed with 1% hydrochloric acid. A 5% copper(II) acetate solution was added to the ether fraction, followed by hexane. The liquid phase was decanted and the remaining gummy solid stirred with 6N HCl and ether. The ether layer was dried (MgSO₄) and concentrated to give 4.7 of a thick yellow solid. Purification on a centrifugally accelerated thin layer chromatograph (4 mm silica gel, 50:50:1 hexane:ethyl acetate:acetic acid--eluent) yielded 2.4 g of a viscous oil which was identified as the desired compound by nmr, ir and ms.

The compounds of Embodiments F and F' of the present invention can be prepared by the following two-step general method.

The process proceeds via the production of an enol ester intermediate as shown in reaction (1). The final product is obtained by rearrangement of the enol ester as shown in reaction (2). The two reactions may be conducted as separate steps by isolation and recovery of the enol ester using conventional techniques prior to conducting step (2), or by addition of a cyanide source to the reaction medium after the formation of the enol ester, or in one step by inclusion of the cyanide source at the start of reaction (1). ##STR62## wherein R⁵⁰ through R⁵⁸ are as defined and X is halogen, preferably chlorine, C₁ -C₄ alkyl-C(O)13 O--, C₁ -C₄ alkoxy-C(O)--O--or ##STR63## wherein R⁵⁰, R⁵⁷ and R⁵⁸ in this portion of the molecule are identical with those in the reactant shown above and the moderate base is as defined, preferably tri-C₁ -C₆ alkylamine, alkali metal carbonate or alkali metal phosphate.

Generally, in step (1) mole amounts of the dione and substituted benzoyl reactant are used, along with a mole amount or excess of the base. The two reactants are combined in an organic solvent such as methylene chloride, toluene, ethyl acetate or dimethylformamide. The base or benzoyl reactant preferably are added to the reaction mixture with cooling. The mixture is stirred at 0° C.-50° C. until the reaction is substantially complete.

The reaction product is worked up by conventional techniques. ##STR64## wherein R⁵⁰ through R⁵⁸ are as defined.

Generally, in step (2) a mole of the enol ester intermediate is reacted with 1 to 4 moles of the base, preferably about 2 moles of moderate base and from 0.01 mole to about 0.5 mole or higher, preferably around 0.1 mole of the cyanide source (e.g., potassium cyanide or acetone cyanohydrin). The mixture is stirred in a reaction pot until the rearrangement is substantially complete at a temperature below 80° C., preferably about 20° C. to about 40° C., and the desired product is recovered by conventional techniques.

The term "cyanide source" refers to a substance or substances which under the rearrangement conditions consists of or generates hydrogen cyanide and/or cyanide anion.

The process is conducted in the presence of a catalytic amount of a source of cyanide anion and/or hydrogen cyanide, together with a molar excess, with respect to the enol ester, of a moderate base.

Preferred cyanide sources are alkali metal cyanides such as sodium and potassium cyanide; cyanohydrins of methyl alkyl ketones having from 1-4 carbon atoms in the alkyl groups, such as acetone or methyl isobutyl ketone cyanohydrins; cyanohydrins of benzaldehyde or of C₂ -C₅ aliphatic aldehydes such as acetaldehyde, propionaldehyde, etc., cyanohydrins; zinc cyanide; tri(lower alkyl) silyl cyanides, notably trimethyl silyl cyanide; and hydrogen cyanide itself. Hydrogen cyanide is considered most advantageous as it produces relatively rapid reaction and is inexpensive. Among cyanohydrins the preferred cyanide source is acetone cyanohydrin.

The cyanide source is used in an amount up to about 50 mole percent based on the enol ester. It may be used in as little as about 1 mole percent to produce an acceptable rate of reaction at about 40° C. on a small scale. Larger scale reactions give more reproducible results with slightly higher catalyst levels of about 2 mole percent. Generally about 1-10 mole % of the cyanide source is preferred.

The process is conducted with a molar excess, with respect to the enol ester, of a moderate base. By the term "moderate base" is meant a substance which acts as a base yet whose strength or activity as a base lies between that of strong bases such as hydroxides (which could cause hydrolysis of the enol ester) and that of weak bases such as bicarbonates (which would not function effectively). Moderate bases suitable for use in this embodiment include both organic bases such as tertiary amines and inorganic bases such as alkali metal carbonates and phosphates. Suitable tertiary amines include trialkylamines such as triethylamine. Suitable inorganic bases include potassium carbonate and trisodium phosphate.

The base is used in an amount of from about 1 to about 4 moles per mole of enol ester, preferably about 2 moles per mole.

When the cyanide source is an alkali metal cyanide, particularly potassium cyanide, a phase transfer catalyst may be included in the reaction. Particularly suitable phase transfer catalysts are the Crown ethers.

A number of different solvents may be usable in this process, depending on the nature of the acid chloride or the acylated product. A preferred solvent for this reaction is 1,2-dichloroethane. Other solvents which may be employed, depending on the reactants or products include toluene, acetonitrile, methylene chloride, ethyl acetate, dimethylformamide, and methyl isobutyl ketone (MIBK).

In general, depending on the nature of the reactants and the cyanide source, the rearrangment may be conducted at temperatures up to about 50° C.

The above described substituted benzoyl chlorides can be prepared from the corresponding substituted benzoic acids according to the teaching of Reagents for Organic Synthesis, Vol. I, L. F. Fieser and M. Fieser, pp. 767-769 (1967). ##STR65## wherein R⁵⁰, R⁵⁷ and R⁵⁸ are as previously defined.

The substituted benzoic acids can be prepared by a wide variety of general methods according to the teaching of The Chemistry of Carboxylic Acids and Esters, S. Patai, editor, J. Wiley and Sons, New York, N.Y. (1969) and Survey of Organic Synthesis, C. A. Buehler and D. F. Pearson, J. Wiley and Sons, (1970).

The following are four representative examples of the methods described therein. ##STR66## wherein R⁵⁰, R⁵⁷ and R⁵⁸ are as previously defined.

In reaction (a) the substituted benzonitrile is heated to reflux in aqueous sulfuric acid for several hours. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR67## wherein R⁵⁰, R⁵⁷ and R⁵⁸ are as previously defined.

In reaction (b) the substituted acetophenone is heated to reflux for several hours in an aqueous hypochlorite solution. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR68## wherein R⁵⁰, R⁵⁷ and R⁵⁸ are as defined and X is chlorine, bromine or iodine.

The substituted aromatic halide is allowed to react with magnesium in a solvent such as ether. The solution is then poured over crushed dry ice and the benzoic acid is isolated by conventional techniques.

The following example teachs the synthesis of a representative compound of Embodiments F and F' of this invention.

EXAMPLE 1-F,F' 2-(4'-Bromo-2'-trifluoromethylbenzoyl)-4,46-trimethyl-1,3-cyclohexanedione ##STR69##

4-Bromo-2-trifluoromethylbenzoyl chloride (4.3 g, 15 mmol) and 4,46-trimethyl-1,3-cyclohexanedione (2.3 g, 15 mmol) were dissolved in 100 ml methylene chloride. The solution was cooled with an ice bath and triethylamine (2.1 ml, 15 mmol) in 10 methylene chloride was added dropwise. The ice bath was then removed and the resulting solution stirred for 30 minutes at room temperature. The solution was washed with 2N hydrochloric acid (2N HCl), 5% potassium carbonate solution (5% K₃ CO₃) and saturated sodium chloride solution (brine), dried over anhydrous magnesium sulfate (MgSO₄) and concentrated under vacuum. The residue (5.1g) was dissolved in 20 ml acetonitrile. Triethylamine (3.5 ml, 25 mmol) and 0.4 ml acetone cyanohydrin were added and the solution stirred for two hours at room temperature while protected by a drying tube (calcium sulfate). After dilution with ether, the solution was washed with 2N HCl and extracted with 5% K.sub. 2 CO₃. The aqueous extract was acidified with concentrated hydrochloric acid and extracted with ether. The ether was washed with brine, dried (MgSO₄) and concentrated under vacuum. The resulting oil was purified on a silica gel column (80:20: 1 hexane:ethyl acetate:acetic acid--eluent), yielding 1.5 g of a viscous oil which was identified as the desired compound by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy.

The compounds of Embodiment G and G' of the present invention can be prepared by the following two-step general method.

The process proceeds via the production of an enol ester intermediate as shown in reaction (1). The final product is obtained by rearrangement of the enol ester as shown in reaction (2). The two reactions may be conducted as separate steps by isolation and recovery of the enol ester using conventional techniques prior to conducting step (2), or by addition of a cyanide source to the reaction medium after the formation of the enol ester, or in one step by inclusion of the cyanide source at the start of reaction (1). ##STR70## wherein R⁶⁰ through R⁶⁶ and moderate base are as defined and X is halogen, preferably chlorine, C₁ -C₄ alkyl-C(O)--O-- C₁ -C₄ alkoxy-C(O)--O-- or ##STR71## wherein R⁶⁰, R⁶⁵ and R⁶⁶ in this portion of the molecule are identical with those in the reactant shown above and the moderate base is as defined, preferably tri-C₁ -C₆ alkylamine, alkali metal carbonate or alkali metal phosphate.

Generally, in step (1) mole amounts of the trione and substituted benzoyl reactant are used, along with a mole amount or excess of the base. The two reactants are combined in an organic solvent such as methylene chloride, toluene, ethyl acetate or dimethylformamide. The base or benzoyl reactant preferably is added to the reaction mixture with cooling. The mixture is stirred at 0° C.-50° C. until the reaction is substantially complete. ##STR72## wherein the moderate base and R⁶⁰ through R⁶⁶ are as defined above.

Generally, in step (2) a mole of the enol ester intermediate is reacted with 1 to 4 moles of the moderate base, preferably about 2 moles of moderate base and from 0.01 mole to about 0.5 mole or higher, preferably about 0.1 mole of the cyanide source (e.g., potassium cyanide or acetone cyanohydrin). The mixture is stirred in a reaction pot until the rearrangement is substantially complete at a temperature below 50° C., preferably about 20° C. to about 40° C., and the desired product is recovered by conventional techniques.

The term "cyanide source" refers to a substance or substances which under the rearrangement conditions consists of or generates hydrogen cyanide and/or cyanide anion.

The process is conducted in the presence of a catalytic amount of a source of cyanide anion and/or hydrogen cyanide, together with a molar excess, with respect to the enol ester, of a moderate base.

Preferred cyanide sources are alkali metal cyanides such as sodium and potassium cyanide; cyanohydrins of methyl alkyl ketones having from 1-4 carbon atoms in the alkyl groups, such as acetone or methyl isobutyl ketone cyanohydrins; cyanohydrins of benzaldehyde or of C₂ -C₅ aliphatic aldehydes such as acetaldehyde, propionaldehyde, etc., cyarohydrins; zinc cyanide; tri(lower alkyl) silyl cyanides, notably trimethyl silyl cyanide; and hydrogen cyanide itself. Hydrogen cyanide is considered most advantageous as it produces relatively rapid reaction and is inexpensive. Among cyanohydrins the preferred cyanide source is acetone cyanohydrin.

The cyanide source is used in an amount up to about 50 mole percent based on the enol ester. It may be used in as little as about 1 mole percent to produce an acceptable rate of reaction at about 40° C. on a small scale. Larger scale reactions give more reproducible results with slightly higher catalyst levels of about 2 mole percent. Generally about 1-10 mole % of the cyanide source is preferred.

The process is conducted with a molar excess, with respect to the enol ester, of a moderate base. By the term "moderate base" is meant a substance which acts as a base yet whose strength or activity as a base lies between that of strong bases such as hydroxides (which could cause hydrolysis of the enol ester) and that of weak bases such as bicarbonates (which would not function effectively). Moderate bases suitable for use in this embodiment include both organic bases, e.g., trialkylamines such as triethylamine and inorganic bases such as alkali metal carbonates and phosphates. Suitable inorganic bases include potassium carbonate and trisodium phosphate.

The base is used in an amount of from about 1 to about 4 moles per mole of enol ester, preferably about 2 moles per mole.

When the cyanide source is an alkali metal cyanide, particularly potassium cyanide, a phase transfer catalyst may be included in the reaction. Particularly suitable phase transfer catalysts are the crown ethers.

A number of different solvents are useful in this process, depending on the nature of the acid halide or the acylated product. A preferred solvent for this reaction is 1,2-dichloroethane. Other solvents which may be employed, depending on the reactants or products include toluene, acetonitrile, methylene chloride, ethyl acetate, dimethylformamide, and methyl isobutyl ketone (MIBK).

In general, depending on the nature of the reactants and the cyanide source, the rearrangment may be conducted at temperatures up to about 50° C.

The above described substituted benzoyl chlorides can be prepared from the corresponding substituted benzoic acids according to the teaching of Reagents for Organic Synthesis, Vol. L. F. Fieser and M. Fieser, pp. 767-769 (1967). ##STR73## wherein R⁶⁰, R⁶⁵ and R⁶⁶ are as previously defined.

The substituted benzoic acids can be prepared by a wide variety of general methods according to the teaching of The Chemistry of Carboxylic Acids and Esters, S. Patai, editor, J. Wiley and Sons, New York, N.Y. (1969) and Survey of Organic Synthesis, C. A. Buehler and D. F. Pearson, J. Wiley and Sons, (1970).

The following are three representative examples of the methods described therein. ##STR74## wherein R⁶⁰, R⁶⁵ and R⁶⁶ are as previously defined.

In reaction (a) the substituted benzonitrile is heated to reflux in aqueous sulfuric acid for several hours. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR75## wherein R⁶⁰, R⁶⁵ and R⁶⁶ are as previously defined.

In reaction (b) the substituted acetophenone is heated to reflux for several hours in an aqueous hypochlorite solution. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR76## wherein R⁶⁰, R⁶⁵ and R⁶⁶ are as previously defined.

In reaction (c) the substituted toluene is heated to reflux in an aqueous solution of potassium permanganate for several hours. The solution is then filtered and the reaction product is isolated by conventional techniques.

The following example teaches the synthesis of a representative compound of Embodiment G and G' of this invention.

EXAMPLE 1-G,G' 2-(2'-Nitro-4'-chlorobenzoyl)-4,4,6,6-tetramethyl-1,3,5-cyclohexanetrione ##STR77##

2-Nitro-4-chlorobenzoyl chloride (2.2 g, 10 mmol) and 4,4,5,6-tetramethyl-1,3,5-cyclohexanetrione (1.8 g, 10 mmol) were dissolved in methylene chloride. Triethylamine was added and the resulting solution stirred at room temprature for 30 minutes. The solution was washed with 1 normal hydrochloric acid (1N HCl), and saturated sodium chloride (brine), dried over anhydrous magnesium sulfate (MgSO₄) and concentrated under vacuum. The residue was dissolved in 20 ml acetonitrile. Triethylamine (5 ml, 3.5 equivalents) and acetone cyanohydrin (0.5 g, 0.6 equivalent) were added and the mixture stirred at room temperature for 4 hours. After dilution with ether, the solution was washed with 1N HCl and extracted with 5% K₂ CO₃. The basic extract was acidified with HCl and extracted with ether. The ether extract was washed with brine, dried over MgSO₄ and concentrated under vacuum, yielding 2.2 g of crude product. This was recrystallized from benzene to remove syncarpic acid still present. Concentration of the mother liquor under vacuum gave 1.7 g of the desired product as an oil, which solidifed on standing (m.p. 76°-82° C.). It was identified as such by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy.

The following are table of certain compounds of Embodiments A-G' that are preparable according to the procedures described herein. Compound numbers are assigned to each compound and are used throughout the remainder of the application.

                                      TABLE I-A                                    __________________________________________________________________________      ##STR78##                                                                     Cmpd.                                          n.sub.D.sup.30 or               No. R         R.sup.1                                                                           R.sup.2                                                                            R.sup.3    R.sup.4   R.sup.5                                                                             m.p. °C.                 __________________________________________________________________________     1A  CH.sub.3  CH.sub.3                                                                          Cl  H          H         H    1.5613                          2A  CH.sub.3  CH.sub.3                                                                          Cl  H          4-Cl      H    1.5655                          3A  CH.sub.3  CH.sub.3                                                                          Cl  H          H         6-Cl 103-108                         4A* H         H  Cl  H          4-Cl      H    138-140                         5A  CH.sub.3  CH.sub.3                                                                          Br  H          H         H                                    6A  CH.sub.3  CH.sub.3                                                                          Cl  H          H         5-Cl 74-77                           7A  H         H  Cl  H          H         5-Cl 104-107                         8A  H         H  Br  H          H         H    93-96                           9A  H         H  Cl  H          H         H    79-87                           10A H         H  I   H          H         H    66-70                           11A H         H  Cl  H          4-NO.sub.2                                                                               H    118-122                         12A H         H  Cl  H          H         6-Cl 143-148                         13A H         H  Cl  H          H         5-Br 109-115                         14A H         H  I   3-I        H         5-I  164-167                         15A H         H  Cl  H          H         5-CH.sub.3                                                                          60-65                           16A H         H  Cl  H          4-CH.sub.3                                                                               H    79-86                           17A H         H  Cl  H          4-CH.sub.3 O                                                                             H    60-63                           18A H         H  Cl  3-Cl       H         6-Cl                                 19A H         H  Cl  H          H         5-CH.sub.3 O                                                                        77-80                           20A H         H  Cl  3-Cl       H         H    80-90                           21A H         H  Cl  H          H         5-CF.sub.3                                                                          74-75                           22A H         H  Cl  H          H         5-NO.sub.2                                                                          140-143                         23A H         H  Cl  3-Cl       4-Cl      H    152-154                         24A H         H  Cl  3-Cl       4-CH.sub.3 O                                                                             H    169-170                         25A H         H  Cl  H          4-Br      H    104-107                         26A CH.sub.3  CH.sub.3                                                                          CH.sub.3 O                                                                         H          H         H    104-108                         27A H         H  Cl  H                                                                                          ##STR79##                                                                               H                                    28A H         H  Br  H          H         (a)                                  29A H         H  CH.sub.3 O                                                                         3-CH.sub.3 O                                                                              H         H    75-79                           30A H         H  CH.sub.3 O                                                                         H          H         5-CH.sub.3 O                                                                        89- 92                          31A H         H  Br  H          4-CH.sub.3 O                                                                             5-CH.sub.3 O                                                                        92-96                           32A H         H  Br  H          (4)OCH.sub.2 O(5)                                                                             63-68                           33A CH.sub.3  CH.sub.3                                                                          Cl  3-Cl       4-Cl      H    86-89                           34A H         H  Cl  3-Cl       H         5-Cl                                 35A CH.sub.3  CH.sub.3                                                                          Cl  3-Cl       H         5-Cl 105-109                         36A CH.sub.3  CH.sub.3                                                                          Cl  3-Cl       4-Cl      5-Cl 137-139                         37A H         H  Cl  3-Cl       4-Cl      5-Cl 106-110                         38A H         H  Cl  H          4-Cl      5-Cl 108-111                         39A                                                                                 ##STR80##                                                                               H  Cl  H          4-Cl      H                                    40A                                                                                 ##STR81##                                                                               H  Cl  H          4-Cl      H                                    41A CH(CH.sub.3).sub.2                                                                       H  Cl  H          4-Cl      H                                    42A CH(CH.sub.3).sub.2                                                                       H  Cl  3-Cl       4-Cl      H                                    43A H         H  Cl  H          4-F       H                                    44A sodium salt of Compound No. 23             85-94                           45A isopropylamine salt of Compound No. 23     160-165                         46A triethylamine salt of Compound No. 23      82-85                           47A potassium salt of Compound No. 23          107-106                         48A triethanolammonium salt of Compound No. 39                                 49A sodium salt of Compound No. 43             60-63                           50A CH(CH.sub.3).sub.2                                                                       H  Cl  3-CH.sub.3 O                                                                              4-Br      H                                    51A H         H  Cl  H          4-CH.sub.3 SO.sub.2                                                                      H    140-141                         52A H         CH.sub.3                                                                          Cl  H          4-Cl      H                                    53A i-C.sub.4 H.sub.9                                                                        H  Cl  H          4-Cl      H                                    54A i-C.sub.3 H.sub.7                                                                        H  Cl  3-CH.sub.3 O                                                                              H         H                                    55A CH.sub.3  CH.sub.3                                                                          Cl  H          4-CH.sub.3 SO.sub.2                                                                      H                                    56A CH.sub.3  CH.sub.3                                                                          Cl  3-CH.sub.3 4-Cl      H                                    57A H         H  Cl  3-CH.sub.3 4-Cl      H    56-64                           58A H         H  Cl  H          4-C.sub.2 H.sub.5 SO.sub.2                                                               H    98-102                          59A H         H  Cl  3-Cl       4-C.sub.2 H.sub.5 SO.sub.2                                                               H    98-109                          60A H         H  Cl  H          4-C.sub.3 H.sub.7 SO.sub.2                                                               H    semi-solid                      61A H         H  Cl  3-CH.sub.3 O                                                                              4-CH.sub.3 SO.sub.2                                                                      H    48-59                           62A CH.sub.3  CH.sub.3                                                                          Cl  H          4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H    semi-solid                      63A H         H  Cl  3-Cl       4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H      145-148.5                     64A H         H  Cl  3-C.sub.2 H.sub. 5 S                                                                      4-C.sub.2 H.sub.5 SO.sub.2                                                               H    oil                             65A CH.sub.3  CH.sub.3                                                                          Cl  H          4-C.sub.2 H.sub.5 SO.sub.2                                                               H    103-108                         66A CH.sub.3  CH.sub.3                                                                          Cl  3-Cl       4-C.sub.2 H.sub.5 SO.sub.2                                                               H    108-114                         67A i-C.sub.3 H.sub.7                                                                        H  Cl  H          4-C.sub.2 H.sub.5 SO.sub.2                                                               H    brown gum                       68A H         H  Cl  3-Cl       4-CH.sub.3 SO.sub.2                                                                      H    145-154                         69A i-C.sub.3 H.sub.7                                                                        H  Cl  3-Cl       4-CH.sub.3 SO.sub.2                                                                      H                                    70A H         H  Br  H          4-CH.sub.3 SO.sub.2                                                                      H    brown gum                       71A H         H  Cl  H          4-i-C.sub.3 H.sub.7 SO.sub.2                                                             H    semi-solid                      72A H         H  Cl  H          4-CH.sub.3 S                                                                             H    74-77                           73A H         H  Cl  3-Cl       4-CH.sub.3 S                                                                             H                                    74A CH.sub.3  CH.sub.3                                                                          Cl  3-Cl       4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H    120-123                         75A H         H  Cl  H          4-n-C.sub.4 H.sub.9 SO.sub.2                                                             H    semi-solid                      76A CH.sub.3  CH.sub.3                                                                          Cl  H          4-n-C.sub.4 H.sub.9 SO.sub.2                                                             H                                    77A H         H  Cl  3-C.sub.2 H.sub.5 O                                                                       4-CH.sub.3 SO.sub.2                                                                      H    semi-solid                      78A H         H  Cl  3-CH.sub.3 O                                                                              4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H    golden gum                      79A CH.sub.3  CH.sub.3                                                                          Cl  H          4-i-C.sub.3 H.sub.7 SO.sub.2                                                             H    125-128                         80A CH(CH.sub.3).sub.2                                                                       H  CH.sub.3 O                                                                         3-Cl       5-Cl      H                                    81A H         H  Cl  3-CH.sub.3 O                                                                              4-Br      H    101-111                         82A H         H  Cl  3-CH.sub.3 O                                                                              4-Cl      H    56-64                           83A H         H  Cl  H          4-Cl      5-CH.sub.3 O                                                                        softens >70                     84A CH(CH.sub.3).sub.2                                                                       H  Cl  3-n-C.sub.3 H.sub.7 O                                                                     4-Br      H                                    85A H         H  Cl  3-C.sub.2 H.sub.5 O                                                                       4-Br      H    101-104                         86A H         H  Cl  H          4-i-C.sub.4 H.sub.9 SO.sub.2                                                             H    136-140                         87A CH.sub.3  CH.sub.3                                                                          Cl  H          4-i-C.sub.4 H.sub.9 SO.sub.2                                                             H                                    88A H         H  Cl  3-Cl       4-i-C.sub.3 H.sub.7 SO.sub.2                                                             H    173-176                         89A H         H  Cl  3-Cl       4-n-C.sub.4 H.sub.9 SO.sub.2                                                             H    135-138                         90A H         H  Cl  3-C.sub.2 H.sub.5 O                                                                       4-C.sub.2 H.sub.5 SO.sub.2                                                               H    gum                             91A H         H  Cl  3-CH.sub.3 O                                                                              4-C.sub.2 H.sub.5 SO.sub.2                                                               H    gum                             92A H         H  Cl  3-Cl       4-C.sub.2 H.sub.5 S                                                                      H    91-94                           93A H         H  Cl  3-C.sub.2 H.sub.5 S                                                                       4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H    oil                             94A H         H  Cl  3-C.sub.2 H.sub.5 S                                                                       4-C.sub.2 H.sub.5 S                                                                      H    oil                             95A H         H  Cl  H          4-(CH.sub.3).sub.2 NSO.sub.2                                                             H    oil                             96A H         H  Cl  3-C.sub.2 H.sub.5 O                                                                       4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H                                    97A H         H  Cl  3-n-C.sub.3 H.sub.7 O                                                                     4-C.sub.2 H.sub.5 SO.sub.2                                                               H    oil                             98A CH.sub.3  CH.sub.3                                                                          Cl  H          4-(CH.sub.3).sub.2 NSO.sub.2                                                             H    oil                             99A H         H  Cl  H          4-(C.sub.2 H.sub.5).sub.2 NSO.sub.2                                                      H    90-92                           100A                                                                               CH.sub.3  CH.sub.3                                                                          Cl  H          4-(C.sub.2 H.sub.5).sub.2 NSO.sub.2                                                      H                                    101A                                                                               H         H  Cl  H          4-C.sub.2 H.sub.5 S                                                                      H                                    102A                                                                               H         H  Cl  H          4-n-C.sub.3 H.sub.7 S                                                                    H                                    103A                                                                               H         H  Cl  H          4-i-C.sub.3 H.sub.7 S                                                                    H                                    104A                                                                               H         H  Cl  H          4-C.sub.2 H.sub.5 SO                                                                     H                                    105A                                                                               H         H  CH.sub.3 O                                                                         H          4-NO.sub.2                                                                               H    semi-solid                      106A                                                                               H         H  Cl  3-n-C.sub.3 H.sub.7 O                                                                     4-Br      H                                    107A                                                                               H         H  Cl  3-n-C.sub.3 H.sub.7 O                                                                     4-CH.sub.3 SO.sub.2                                                                      H     96-100                         108A                                                                               H         H  Cl  3-allyloxy 4-CH.sub.3 SO.sub.2                                                                      H    semi-solid                      109A                                                                               H         H  Cl  3-CH.sub.3 C(O)NH                                                                         4-Cl      H    155-160                         110A                                                                               H         H  Cl  3-Cl       4-n-C.sub.3 H.sub.7 S                                                                    H                                    111A                                                                               H         H  Cl  3-CH.sub.3 O                                                                              4-NO.sub.2                                                                               H    150-153                         112A                                                                               H         H  Cl  3-allyloxy 4-C.sub.2 H.sub.5 SO.sub.2                                                               H                                    113A                                                                               H         H  Cl  3-CH.sub.2 BrCHBrCH.sub.2 O                                                               4-C.sub.2 H.sub.5 SO.sub.2                                                               H                                    114A                                                                               H         H  Cl  3-n-C.sub.4 H.sub.9 O                                                                     4-C.sub.2 H.sub.5 SO.sub.2                                                               H    gum                             115A                                                                               H         H  Cl  3-i-C.sub.4 H.sub.9 O                                                                     4-C.sub.2 H.sub.5 SO.sub.2                                                               H                                    116A                                                                               H         H  Cl  H          4-allylthio                                                                              H                                    117A                                                                               CH.sub.3  CH.sub.3                                                                          Cl  H          4-NO.sub.2                                                                               H                                    118A                                                                               H         H  Cl  3-CH.sub.3 C(O)N(CH.sub.3)                                                                4-Cl      H                                    119A                                                                               H         H  Cl  3-i-C.sub.3 H.sub.7 O                                                                     4-C.sub.2 H.sub.5 SO.sub.2                                                               H                                    120A                                                                               H         H  Cl  3-CH.sub.2 ClCH.sub.2 CH.sub.2 O                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                               H    gum                             121A                                                                               H         H  Cl  H          4-t-C.sub.4 H.sub.9 S                                                                    H                                    122A                                                                               H         H  Cl  3-CH.sub.3 O                                                                              4-C.sub.2 H.sub.5 S                                                                      H                                    123A                                                                               H         H  Cl  H          4-CF.sub.3                                                                               H                                    124A                                                                               H         H  Cl  H          4-Cl      6-Cl                                 125A                                                                               H         H  Cl  3-CH.sub.3 C(O)N(CH.sub.3)                                                                H         H    131-135                         126A                                                                               H         H  Cl  3-CH.sub.3 C(O)NH                                                                         H         H                                    127A                                                                               H         H  Cl  3-(CH.sub.3).sub.2 N                                                                      4-Cl      H                                    128A                                                                               CH.sub.3  H  Cl  3-CH.sub.3 O                                                                              4-CH.sub.3 SO.sub.2                                                                      H    117-122                         129A                                                                               H         H  Cl  H          4-C.sub.2 H.sub.5 SO.sub.2                                                               H                                    130A                                                                               H         H  Br  H          H         H                                    131A                                                                               H         H  Br  H          4-C.sub.2 H.sub.5 OC(O)                                                                  H                                    132A                                                                               H         H  Cl  H          4-CN      H    183-184                         133A                                                                               H         H  Cl  3-CH.sub.3 C(O)NH                                                                         H         6-NO.sub.2                           134A                                                                               H         H  Cl  3-(CH.sub.3).sub.2 N                                                                      H         H                                    135A                                                                               H         H  Cl  3-Cl       4-ClCH.sub.2 CH.sub.2 SO.sub.2                                                           H                                    __________________________________________________________________________      * = Prepared in Example 1A.                                                    ##STR82##                                                                      -                                                                        

                                      TABLE I-B                                    __________________________________________________________________________      ##STR83##                                                                     Compound                                                                       Number                                                                               R.sup.10 R.sup.11                                                                           R.sup.12                                                                           R.sup.13                                                                             R.sup.14  R.sup.15                                                                          R.sup.16                                                                          R.sup.17                                                                          R.sup.18                       __________________________________________________________________________     1B                                                                                    ##STR84##                                                                              H   Cl  H     4-Cl      H  H  H  H                              2B                                                                                    ##STR85##                                                                              CH.sub.3                                                                           Cl  H     4-Cl      H  H  H  H                              3B    triethanolammonium salt of Compound No. 2                                4B    triethanolammonium salt of Compound No. 7                                5B                                                                                    ##STR86##                                                                              CH.sub.3                                                                           Cl  3-Cl  4-Cl      H  H  H  H                              6B    triethanolammonium salt of Compound No. 5                                7B.sup.(a)                                                                           CH.sub.3 CH.sub.3                                                                           Cl  H     4-Cl      H  H  H  H                              8B    CH.sub.3 CH.sub.3                                                                           Cl  H     4-Cl      CH.sub.3                                                                          H  H  H                              9B    CH.sub.3 n-C.sub.3 H.sub.7                                                                  Cl  H     4-Cl      H  H  H  H                              10B   CH.sub.3 H   Cl  H     4-Cl      H  H  H  H                              11B   CH.sub.3 H   Cl  H     4-Cl      CH.sub.3                                                                          H  H  H                              12B   C.sub.5 H.sub.10                                                                            Cl  H     4-Cl      H  H  H  H                              13B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-Cl      H  H  H  H                              14B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-Cl      CH.sub.3                                                                          H  H  H                              15B   i-C.sub.3 H.sub.7                                                                       H   Cl  3-Cl  4-Cl      H  H  H  H                              16B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-CH.sub.3 SO.sub.2                                                                      H  H  H  H                              17B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-CH.sub.3 SO.sub.2                                                                      CH.sub.3                                                                          H  H  H                              18B   CH.sub.3 H   Cl  H     4-CH.sub.3 SO.sub.2                                                                      H  H  H  H                              19B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-CH.sub.3 SO.sub.2                                                                      H  H  H  H                              20B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-C.sub.2 H.sub.5 SO.sub.2                                                               H  H  H  H                              21B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-C.sub.2 H.sub.5 SO.sub.2                                                               H  H  H  H                              22B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-C.sub.2 H.sub.5 SO.sub.2                                                               CH.sub.3                                                                          H  H  H                              23B   CH.sub.3 CH.sub.3                                                                           Cl  3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                               H  H  H  H                              24B   CH.sub.3 CH.sub.3                                                                           Cl  3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                      H  H  H  H                              25B   CH.sub.3 CH.sub.3                                                                           Cl  3-CH.sub.3                                                                           4-Cl      H  H  H  H                              26B   CH.sub.3 CH.sub.3                                                                           Cl  3-OCH.sub.3                                                                          4-Cl      H  H  H  H                              27B   CH.sub.3 C.sub.2 H.sub.5                                                                    Cl  H     4-Cl      H  H  H  H                              28B   CH.sub.3 CH.sub.3                                                                           Cl  H     H         H  H  H  H                              29B   CH.sub.3 CH.sub.3                                                                           Cl  3-OCH.sub.3                                                                          4-Br      H  H  H  H                              30B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-Br      H  H  H  H                              31B   CH.sub.3 C.sub.2 H.sub.5                                                                    Cl  3-Cl  4-Cl      H  H  H  H                              32B   n-C.sub.3 H.sub.7                                                                       H   Cl  H     4-Cl      H  H  H  H                              33B                                                                                   ##STR87##                                                                              n-C.sub.3 H.sub.7                                                                  Cl  H     4-Cl      H  H  H  H                              34B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-i-C.sub.3 H.sub.7 SO.sub.2                                                             H  H  H  H                              35B   CH.sub.3 CH.sub.3                                                                           Cl  3-i-C.sub.3 H.sub.7 O                                                                4-Br      H  H  H  H                              36B   CH.sub.3 CH.sub.3                                                                           Cl  H     6-F       H  H  H  H                              37B   i-C.sub.3 H.sub.7                                                                       H   Cl  3-Cl  4-Cl      H  H  H  H                              38B   CH.sub.3 CH.sub.3                                                                           Cl  3-OC.sub.2 H.sub.5                                                                   4-Br      CH.sub.3                                                                          H  H  H                              39B   i-C.sub.3 H.sub.7 OC(O)                                                                 H   Cl  H     4-Cl      H  H  H  H                              40B   C.sub.2 H.sub.5 OC(O)                                                                   n-C.sub.3 H.sub.7                                                                  Cl  H     4-Cl      H  H  H  H                              41B   C.sub.5 H.sub.10                                                                            Cl  H     4-Cl      H  H  H  H                              42B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-Cl      H  H  CH.sub.3                                                                          H                              43B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H  H  H  H                              44B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H  H  H  H                              45B   CH.sub.3 CH.sub.3                                                                           CH.sub.3 O                                                                         3-CH.sub.3 O                                                                         H         H  H  H  H                              46B   CH.sub.3 CH.sub.3                                                                           CH.sub.3 O                                                                         H     4-Cl      H  H  H  H                              47B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-Br      CH.sub.3                                                                          H  H  H                              48B   CH.sub.3 CH.sub.3                                                                           Br  H     H         H  H  H  H                              49B   CH.sub.3 CH.sub.3                                                                           I   H     H         H  H  H  H                              50B   CH.sub.3 CH.sub.3                                                                           F   H     H         H  H  H  H                              51B   CH.sub.3 CH.sub.3                                                                           CH.sub.3 O                                                                         H     H         H  H  H  H                              52B   CH.sub.3 CH.sub.3                                                                           Cl  3-allyloxy                                                                           4-Br      H  H  H  H                              53B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-CH.sub.3 SO.sub.2                                                                      H  H  CH.sub.3                                                                          H                              54B   CH.sub.3 CH.sub.3                                                                           Cl  3-CH.sub.3 O                                                                         4-Br      CH.sub.3                                                                          H  H  H                              55B   CH.sub.3 CH.sub.3                                                                           Br  H     4-CN      H  H  H  H                              56B   CH.sub.3 CH.sub.3                                                                           Cl  H     4N(CH.sub.3)SO.sub.2 CF.sub.3                                                            H  H  H  H                              57B   CH.sub.3 CH.sub.3                                                                           Cl  3-NO.sub.2                                                                           H         H  H  H  H                              58B   CH.sub.3 CH.sub.3                                                                           C.sub.2 H.sub.5 O                                                                  H     4-Cl      H  H  H  H                              59B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-i-C.sub.4 H.sub.9 SO.sub.2                                                             H  H  H  H                              60B   CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 O                                                                  4-CH.sub.3 SO.sub.2                                                                      H  H  H  H                              61B   CH.sub.3 CH.sub.3                                                                           Cl  3-CH.sub.3 O                                                                         4-C.sub.2 H.sub.5 SO.sub.2                                                               H  H  H  H                              62B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-n-C.sub.4 H.sub.9 SO.sub.2                                                             H  H  H  H                              63B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-n-C.sub.4 H.sub.9 SO.sub.2                                                             CH.sub.3                                                                          H  H  H                              64B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-C.sub.2 H.sub.5 SO.sub.2                                                               CH.sub.3                                                                          H  H  H                              65B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-F       H  H  H  H                              66B   CH.sub.3 H   Cl  3-CH.sub.3 O                                                                         4-Br      H  H  H  H                              67B   CH.sub.3 CH.sub.3                                                                           Cl  3-CH.sub.3 O                                                                         H         H  H  H  H                              68B   CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 S                                                                  4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H  H  H  H                              69B   CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 S                                                                  4-C.sub.2 H.sub.5 S                                                                      H  H  H  H                              70B   CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 S                                                                  4-C.sub.2 H.sub.5 SO.sub.2                                                               H  H  H  H                              71B   CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 S                                                                  4-CH.sub.3 SO.sub.2                                                                      H  H  H  H                              72B   CH.sub.3 CH.sub.3                                                                           Cl  Cl    4-i-C.sub.3 H.sub.7 SO.sub.2                                                             H  H  H  H                              73B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-n-C.sub.4 H.sub.9 SO.sub.2                                                             H  H  H  H                              74B   CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 O                                                                  4-C.sub.2 H.sub.5 SO.sub.2                                                               H  H  H  H                              75B   CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 O                                                                  4-Br      H  H  H  H                              76B   CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 O                                                                  4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H  H  H  H                              77B   CH.sub.3 CH.sub.3                                                                           Cl  3-n-C.sub.3 H.sub.7 O                                                                4-C.sub.2 H.sub.5 SO.sub.2                                                               H  H  H  H                              78B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-(CH.sub.3).sub.2 NSO.sub.2                                                             H  H  H  H                              79B   CH.sub.3 CH.sub.3                                                                           Cl  3-CH.sub.3 S                                                                         4-C.sub.2 H.sub.5 SO.sub.2                                                               H  H  H  H                              80B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-C.sub.2 H.sub.5 S                                                                      H  H  H  H                              81B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-C.sub.2 H.sub.5 S                                                                      H  H  H  H                              82B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-(C.sub.2 H.sub.5).sub.2 NSO.sub.2                                                      H  H  H  H                              83B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H  H  H  H                              84B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-n-C.sub.3 H.sub.7 S                                                                    CH.sub.3                                                                          H  H  H                              85B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-C.sub.2 H.sub.5 S(O)                                                                   H  H  H  H                              86B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-i-C.sub.3 H.sub.7 S                                                                    H  H  H  H                              87B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-n-C.sub.3 H.sub.7 S                                                                    H  H  H  H                              88B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-t-C.sub.4 H.sub.9 SO.sub.2                                                             H  H  H  H                              89B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-i-C.sub.3 H.sub.7 S                                                                    CH.sub.3                                                                          H  H  H                              90B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-n-C.sub.3 H.sub.7 SO.sub.2                                                             CH.sub.3                                                                          H  H  H                              91B   CH.sub.3 CH.sub.3                                                                           Cl  *     4-Cl      H  H  H  H                              92B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-CH.sub.2CHCH.sub.2 S                                                                   H  H  H  H                              93B   CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 O                                                                  4-C.sub.2 H.sub.5 S                                                                      H  H  H  H                              94B   CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-CH.sub.3 S                                                                             CH.sub.3                                                                          H  H  H                              95B   CH.sub.3 CH.sub.3                                                                           Cl  H     4-CH.sub.3 S                                                                             H  H  H  H                              96B   CH.sub.3 CH.sub.3                                                                           Cl  3-i-C.sub.3 H.sub.7 O                                                                4-C.sub.2 H.sub.5 SO.sub.2                                                               H  H  H  H                              97B   CH.sub.3 CH.sub.3                                                                           Cl  3-CH.sub.3 O                                                                         4-C.sub.2 H.sub.5 S                                                                      H  H  H  H                              98B   CH.sub.3 CH.sub.3                                                                           Cl  **    4-Cl      H  H  H  H                              99B   CH.sub.3 CH.sub.3                                                                           Cl  **    H         H  H  H  H                              100B  CH.sub.3 CH.sub.3                                                                           Cl  3-Cl  4-CH.sub.3 S                                                                             H  H  H  H                              101B  CH.sub.3 CH.sub.3                                                                           CH.sub.3 O                                                                         H     4-NO.sub.2                                                                               H  H  H  H                              102B  CH.sub.3 CH.sub.3                                                                           CH.sub.3 O                                                                         H     4-CF.sub.3                                                                               H  H  H  H                              103B  CH.sub.3 CH.sub.3                                                                           Cl  H     4-n-C.sub.3 H.sub.7 SO                                                                   H  H  H  H                              104B  CH.sub.3 CH.sub.3                                                                           Cl  H     4-n-C.sub.3 H.sub.7 SO                                                                   CH.sub.3                                                                          H  H  H                              __________________________________________________________________________      (a) Prepared in Example IB.                                                    * = 3CH.sub.3 C(O)NH                                                           ** = 3CH.sub.3 C(O)N(CH.sub.3)                                           

The following additional compounds can be prepared by the general method hereinbefore taught.

                                      TABLE I-B                                    __________________________________________________________________________      ##STR88##                                                                     R.sup.10                                                                            R.sup.11                                                                            R.sup.12                                                                           R.sup.13                                                                              R.sup.14                                                                              R.sup.15                                                                           R.sup.16                                                                           R.sup.17                                                                           R.sup.18                               __________________________________________________________________________     CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  H      4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  H      4-Cl   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  H      4-Cl   CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  H      4-Cl   H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  H      4-Cl   CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  H      4-Cl   H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  H      4-Cl   CH.sub.3                                                                           H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  H      4-Cl   H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  H      4-Cl   CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  H      4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-Cl   4-Cl   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-Cl   4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-Cl   4-Cl   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-Cl   4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  3-Cl   4-Cl   H   H   H   H                                      CH.sub.3                                                                            H    Cl  3-Cl   4-Cl   CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-Cl   4-Cl   H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-Cl   4-Cl   CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-Cl   4-Cl   H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-Cl   4-Cl   CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-Cl   4-Cl   H   H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-Cl   4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  H      4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  H      4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  H      4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  H      4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  H      4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  H      4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  H      4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  H      4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  H      4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  H      4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  H      4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  H      4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  H      4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            H    Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            H    Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub. 5                                                                    H    Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub. 9                                                                  Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            H    Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            H    Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      CH.sub.3                                                                            H    Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                             H  H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-CH.sub.3                                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            H    Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub. 2                                                                  CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      CH.sub.3                                                                            H    Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                       H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-CH.sub.3                                                                            4-CH.sub.3 SO.sub.2                                                                   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-CH.sub.3                                                                            4-Cl   CH.sub.3                                                                           H   H    H                                     CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-CH.sub.3                                                                            4-Cl   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-CH.sub.3                                                                            4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-CH.sub.3                                                                            4-Cl   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-CH.sub.3                                                                            4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  3-CH.sub.3                                                                            4-Cl   H   H   H   H                                      CH.sub.3                                                                            H    Cl  3-CH.sub.3                                                                            4-Cl   CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-CH.sub.3                                                                            4-Cl   H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-CH.sub.3                                                                            4-Cl   CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-CH.sub.3                                                                            4-Cl   H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-CH.sub.3                                                                            4-Cl   CH.sub.3                                                                           H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-CH.sub.3                                                                            4-Cl   H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-CH.sub.3                                                                            4-Cl   Ch.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-CH.sub.3                                                                            4-Cl   H   H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-CH.sub.3                                                                            4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-OCH.sub.3                                                                           4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-OCH.sub.3                                                                           4-Cl   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.3 H.sub.7                                                                   Cl  3-OCH.sub.3                                                                           4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-OCH.sub.3                                                                           4-Cl   H   H   H   H                                      CH.sub.3                                                                            n-C.sub.4 H.sub.9                                                                   Cl  3-OCH.sub.3                                                                           4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            H    Cl  3-OCH.sub.3                                                                           4-Cl   H   H   H   H                                      CH.sub.3                                                                            H    Cl  3-OCH.sub.3                                                                           4-Cl   CH.sub.3                                                                           H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-OCH.sub.3                                                                           4-Cl   H   H   H   H                                      C.sub.2 H.sub.5                                                                     H    Cl  3-OCH.sub.3                                                                           4-Cl   CH.sub.3                                                                           H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-OCH.sub.3                                                                           4-Cl   H   H   H   H                                      n-C.sub.4 H.sub.9                                                                   H    Cl  3-OCH.sub.3                                                                           4-Cl   CH.sub.3                                                                           H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-OCH.sub.3                                                                           4-Cl   H   H   H   H                                      i-C.sub.3 H.sub.7                                                                   H    Cl  3-OCH.sub.3                                                                           4-Cl   CH.sub.3                                                                           H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-OCH.sub.3                                                                            4-Cl  H   H   H   H                                      C.sub.5 H.sub.10                                                                         Cl  3-OCH.sub.3                                                                           4-Cl   CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-n-C.sub.3 H.sub.7 O                                                                 4-Br   H   H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                            CH.sub.3                                                                           H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  H      4-NO.sub.2                                                                            H   H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-C.sub.2 H.sub.5 O                                                                   4-CH.sub.3 S                                                                          H   H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  H      4-CN   H   H   H   H                                      CH.sub.3                                                                            CH.sub.3                                                                            Cl  3-(CH.sub.3).sub.2 N                                                                  H      H   H   H                                          __________________________________________________________________________

                                      TABLE I-C                                    __________________________________________________________________________      ##STR89##                                                                     Comp.                                                                          No.  R.sup.21                                                                           R.sup.22                                                                           R.sup.23                                                                          R.sup.24                                                                          R.sup.25                                                                          R.sup.26                                                                          R.sup.27                                                                          R.sup.28                                                                          n.sub.D.sup.30 or m.p.                          __________________________________________________________________________     1C.sup.a                                                                            CH.sub.3                                                                           CH.sub.3                                                                           H  H  H  H  H  H  oil                                             2C   H   H   H  H  H  H  H  CN 124-140° C.                              __________________________________________________________________________      .sup. a Prepared in Example IC.                                          

                                      TABLE I-D                                    __________________________________________________________________________      ##STR90##                                                                     Comp.                                                                          No. R.sup.31                                                                          R.sup.32                                                                           R.sup.33                                                                           R.sup.34                                                                          R.sup.35                                                                          R.sup.36                                                                          R.sup.37                                                                            R.sup.38 n.sub.D.sup.30 or                        __________________________________________________________________________                                           m.p.                                     1D  CH.sub.3                                                                          H   H   H  H  H  H    H        viscous oil                              2D  CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  H    H        viscous oil                              3D.sup.a                                                                           H  H   H   H  H  H  H    H        132-135                                  4D  CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    H        viscous oil                              5D.sup.b                                                                           H  H   CH.sub.3                                                                           CH.sub.3                                                                          H  H  H    H        130-133                                  6D  CH.sub.3                                                                          H   H   H  CH.sub.3                                                                          H  H    H        viscous oil                              7D  CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    CF.sub.3 52-61                                    8D  H  H   H   H  H  H  H    CF.sub.3 88-94                                    9D  H  H   CH.sub.3                                                                           CH.sub.3                                                                          H  H  H    CF.sub.3 89-97                                    10D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  3-CH.sub.3                                                                          H        119-122                                  11D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  3-Cl H        72-79                                    12D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    Cl       118-121                                  13D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  5-Cl H        118-120                                  14D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  5-F  H        130-133                                  15D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  3-CH.sub.3 O                                                                        H        139-142                                  16D CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                                                           H  H  H  H    CF.sub.3 viscous oil                              17D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    NO.sub.2 viscous oil                              18D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    Br       viscous oil                              19D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  CH.sub.3                                                                          5-CH.sub.3                                                                          H        viscous oil                              20D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  5-CH.sub.3                                                                          H        viscous oil                              21D H  H   H   H  H  H  H    F        123-128                                  22D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    F        viscous oil                              23D H  H   H   H  H  H  H    Cl       viscous oil                              24D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SO.sub.2 CH.sub.3                                                                       130-133                                  25D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SO.sub.2n-C.sub.3 H.sub.7                                                               viscous oil                              26D H  H   H   H  H  H  H    SO.sub.2 CH.sub.3                                                                       157-159                                  27D H  H   H   H  H  H  H    SO.sub.2n-C.sub.3 H.sub.7                                                               120-123                                  28D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  5-F  H        165-195                                  29D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SO.sub.2C.sub.2 H.sub.5                                                                 oil                                      30D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  H    SO.sub.2CH.sub.3                                                                        gum                                      31D CH.sub.3                                                                          n-C.sub.4 H.sub.9                                                                  H   H  H  H  H    H        viscous oil                              32D H  H   i-C.sub.4 H.sub.9                                                                  H  H  H  H    H        viscous oil                              33D H  H   H   H  H  H  H    SO.sub.2C.sub.2 H.sub.5                                                                 viscous oil                              34D H  H   H   H  H  H  H    CN       viscous oil                              35D H  H   H   H  H  H  H    SO.sub.2 N(CH.sub.3).sub.2                                                              158-159                                  36D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SO.sub.2 N(CH.sub.3).sub.2                                                              120-130                                  37D H  H   H   H  H  H  H    SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                       158-163                                  38D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                       oil                                      39D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H                                                                                    ##STR91##                                                                              oil                                      40D H  H   CH.sub.3                                                                           CH.sub.3                                                                          H  H  H    SO.sub.2N(C.sub.2 H.sub.5).sub.2                                                        oil                                      41D H  H   H   H  H  H  H    SC.sub.2 H.sub.5                                                                        oil                                      42D H  H   H   H  H  H  H    S(O)n-C.sub.3 H.sub.7                                                                   oil                                      43D H  H   H   H  H  H  H    Sn-C.sub.3 H.sub.7                                                                      oil                                      44D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  H    Sn-C.sub.3 H.sub.7                                                                      oil                                      45D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    Sn-C.sub.3 H.sub.7                                                                      oil                                      46D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  H    S-C.sub.2 H.sub.5                                                                       oil                                      47D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SC.sub.2 H.sub.5                                                                        oil                                      47D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SC.sub.2 H.sub.5                                                                        oil                                      48D H  H   H   H  H  H  H    SCH.sub.3                                                                               94-97                                    49D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  H    CF.sub.3 oil                                      50D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SCH.sub.3                                                                               oil                                      51D .sup.c                                                                            H   i-C.sub.3 H.sub.7                                                                  H  H  H  H    H        145-148                                  52D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  5-CH.sub.3 O                                                                        Br       oil                                      53D H  H   CH.sub.3                                                                           CH.sub.3                                                                          H  H  H    Cl       oil                                      54D H  H   H   H  H  H  3-CH.sub.3 O                                                                        Cl       oil                                      55D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  3-CH.sub.3 O                                                                        Cl       oil                                      56D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  H    CH.sub.3 S                                                                              oil                                      57D H  H   H   H  H  H  H                                                                                    ##STR92##                                                                              120-125                                  58D H  H   CH.sub.3                                                                           CH.sub.3                                                                          H  H  H    CN       175-177                                  59D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    CN       151-153                                  60D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  H    CN       oil                                      61D .sup.c                                                                            H   H   H  H  H  H    H        oil                                      62D .sup.d                                                                            H   H   H  H  H  H    H        oil                                      63D H  H   CH.sub.3                                                                           H  H  H  H    Cl       110-115                                  64D H  H   CH.sub.3                                                                           H  H  H  H    SO.sub.2n-C.sub.3 H.sub.7                                                               oil                                      65D .sup.d                                                                            CH.sub.3                                                                           H   H  H  H  H    Cl       oil                                      66D H  H   H   H  H  H  H    SO.sub.2 CHCl.sub.2                                                                     oil                                      67D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SO.sub.2 CHCl.sub.2                                                                     oil                                      68D H  H   H   H  H  H  c    Br       oil                                      69D H  H   H   H  H  H  H    SO.sub.2 CH.sub.2 Cl                                                                    oil                                      70D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SO.sub.2 CH.sub.2 Cl                                                                    wax                                      71D .sup.d                                                                            CH.sub.3                                                                           H   H  H  H  H    H        oil                                      72D H  H   H   H  H  H  C.sub.2 H.sub.5 O                                                                   Cl       oil                                      73D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  CH.sub.3 O                                                                          CF.sub.3 oil                                      __________________________________________________________________________      .sup.a Prepared in Example 1D,D'.                                              .sup.b Prepared in Example 2D,D'.                                               .sup.c = C.sub.2 H.sub.5 OC(O)-                                               .sup.d = i-C.sub.3 H.sub.7 OC(O)-                                        

                                      TABLE I-E                                    __________________________________________________________________________      ##STR93##                                                                     Comp.                                                                          No. n R.sup.40                                                                          R.sup.41                                                                          R.sup.42                                                                          R.sup.43                                                                          R.sup.44                                                                          R.sup.45                                                                          R.sup.46                                                                          R.sup.47                                                                           R.sup.48                                                                              m.p.                                     __________________________________________________________________________     1E  0 CH.sub.3                                                                          H  H  H  H  H  H  H   H      79-81° C.                         2E  0 CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H   H      oil                                      3E.sup.a                                                                           0 CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  CH.sub.3                                                                          H  H   H      oil                                      4E.sup.b                                                                           2 CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  CH.sub.3                                                                          H  H   H      oil                                      5E  0 C.sub.2 H.sub.5                                                                   CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H   H      oil                                      6E  2 C.sub.2 H.sub.5                                                                   CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H   H      oil                                      7E  0 CH.sub.3                                                                          H  H  H  H  H  H  3-Cl                                                                               Cl     59-64° C.                         8E  2 CH.sub.3                                                                          H  H  H  H  H  H  3-Cl                                                                               Cl     116-119° C.                       9E  0 CH.sub.3                                                                          H  H  H  H  H  H  H   CF.sub.3                                                                              102-106° C.                       10E 2 CH.sub.3                                                                          H  H  H  H  H  H  H   CF.sub.3                                                                              oil                                      11E 0 CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H   CF.sub.3                                                                              49-53° C.                         12E 2 CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H   CF.sub.3                                                                              oil                                      13E.sup.c                                                                          1 CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H   CF.sub.3                                                                              oil                                      14E 0 CH.sub.3                                                                          H  H  H  H  H  H  3-Cl                                                                               SCH.sub.3                                                                             105-107° C.                       15E 1 CH.sub.3                                                                          H  H  H  H  H  H  3-Cl                                                                               S(O)CH.sub.3                                                                          oil                                      16E 0 CH.sub.3                                                                          H  H  H  H  H  H  H   SO.sub.2 n-C.sub.3 H.sub.7                                                            oil                                      17E 0 CH.sub.3                                                                          H  H  H  H  H  H  H   SCH.sub.3                                                                             101-103° C.                       18E 2 CH.sub.3                                                                          H  H  H  H  H  H  H   SO.sub.2 n-C.sub.3 H.sub.7                                                            oil                                      19E 2 CH.sub.3                                                                          H  H  H  H  H  H  H   SO.sub.2 CH.sub.3                                                                     194-196° C.                       20E 0 CH.sub.3                                                                          H  H  H  H  H  H  3-CH.sub.3                                                                         H      40-42° C.                         21E 2 CH.sub.3                                                                          H  H  H  H  H  H  3-CH.sub.3                                                                         H      80-86° C.                         __________________________________________________________________________      .sup.a Prepared in Example 1E,E'.                                              .sup.b Prepared in Example 2E,E'.                                              .sup.c Prepared in Example 3E,E'.                                        

                                      TABLE I-F                                    __________________________________________________________________________      ##STR94##                                                                     Comp.                                n.sub.D.sup.30                            No. R.sup.50                                                                          R.sup.51                                                                          R.sup.52                                                                          R.sup.53                                                                           R.sup.54                                                                          R.sup.55                                                                          R.sup.56                                                                          R.sup.57                                                                           R.sup.58                                                                              or m.p.                                   __________________________________________________________________________     1F  CH.sub.3                                                                          H  H  H   H  H  H  H   H      35-42° C.                          2F  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   H      47-53° C.                          3F  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   Br     oil                                       4F  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   CN     oil                                       5F  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  3-NO.sub.2                                                                         H      oil                                       6F  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  5-Cl                                                                               H      oil                                       7F  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   CH.sub.3 SO.sub.2                                                                     oil                                       8F  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  CH.sub.3                                                                          H  H   CH.sub.3 SO.sub.2                                                                     oil                                       9F  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  3-Cl                                                                               H      oil                                       10F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  CH.sub.3                                                                          H  H   C.sub.2 H.sub.5 SO.sub.2                                                              oil                                       11F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   C.sub.2 H.sub.5 SO.sub.2                                                              oil                                       12F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   n-C.sub.3 H.sub.7 SO.sub.2                                                            oil                                       13F CH.sub.3                                                                          H  H  H   H  H  H  H   CH.sub.3 SO.sub.2                                                                     oil                                       14F CH.sub.3                                                                          H  H  H   H  H  H  H   n-C.sub.3 H.sub.7 SO.sub.2                                                            oil                                       15F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   CH.sub.3 S                                                                            oil                                       16F C.sub.2 H.sub.5                                                                   CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   Br     oil                                       17F CH.sub.3                                                                          H  H  H   H  H  H  H   CN     oil                                       18F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   F      oil                                       19F CH.sub.3                                                                          H  H  H   H  H  H  H   C.sub.2 H.sub.5 SO.sub.2                                                              oil                                       20F CH.sub.3                                                                          H  H  H   H  H  H  3-Cl                                                                               H      65-67° C.                          21F CH.sub.3                                                                          H  H  H   H  H  H  3-I H      oil                                       22F CH.sub.3                                                                          H  H  H   H  H  H  3-NO.sub.2                                                                         H      oil                                       23F CH.sub.3                                                                          H  H  H   H  H  H  3-CN                                                                               H       96-101° C.                        24F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   H      oil                                       25F CF.sub.3                                                                          H  H  H   H  H  H  H   H      oil                                       26F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   Br     oil                                       27F CF.sub.3                                                                          H  H  H   H  H  H  H   Cl     82-88° C.                          28F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   Cl     oil                                       29F CF.sub.3                                                                          H  H  H   H  H  H  H   C.sub.2 H.sub.5 S                                                                     oil                                       30F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   C.sub.2 H.sub.5 SO.sub.2                                                              oil                                       31F CF.sub.3                                                                          H  H  H   H  H  H  H   CN     oil                                       32F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   CN     oil                                       33F.sup.a                                                                          CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  CH.sub.3                                                                          H  H   Br     oil                                       34F CH.sub.3                                                                          H  H  H   H  H  H  H   CH.sub.3                                         35F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  3-Cl                                                                               C.sub.2 H.sub.5 SO.sub.2                                                              115-117° C.                        36F CH.sub.3                                                                          H  H  H   H  H  H  3-Cl                                                                               C.sub.2 H.sub.5 SO.sub.2                                                              oil                                       37F CH.sub.3                                                                          .sup.b                                                                            .sup.b                                                                            H   H  H  H  3-CF.sub.3                                                                         H      oil                                       38F CH.sub.3                                                                          .sup.c                                                                            H  i-C.sub.3 H.sub.7                                                                  H  H  H  3-NO.sub.2                                                                         H       88-108° C.                        39F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  CH.sub.3                                                                          H  H   CH.sub.3 S                                                                            oil                                       40F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   CH.sub.3 S                                                                            oil                                       41F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  CH.sub.3                                                                          H  H   CH.sub.3 SO.sub.2                                                                     oil                                       42F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   CF.sub.3                                                                              oil                                       43F CH.sub.3                                                                          H  H  H   H  H  H  H   CF.sub.3                                                                              114-120° C.                        44F CH.sub.3                                                                          H  H  H   H  H  H  3-Cl                                                                               Cl     oil                                       45F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  3-Cl                                                                               Cl     oil                                       46F CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  3-CF.sub.3                                                                         H      oil                                       47F CF.sub.3                                                                          H  H  H   H  H  H  H   CH.sub.3 S                                                                            oil                                       48F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  CH.sub.3                                                                          H  H   CF.sub.3                                                                              oil                                       49F CF.sub.3                                                                          H  H  H   H  H  H  H   CF.sub.3                                                                              oil                                       50F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  H  H  H   CF.sub.3                                                                              oil                                       51F CH.sub.3                                                                          H  H  CH.sub.3                                                                           H  H  H  H   CH.sub.3 SO.sub.2                                                                     oil                                       52F CF.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H   H  CH.sub.3                                                                          H  H   C.sub.2 H.sub.5 SO.sub.2                                                              oil                                       53F CH.sub.3                                                                          H  H  H   H  H  H  H   Br     94-98° C.                          54F CH.sub.3                                                                          H  H  H   H  H  H  .sup.d                                                                             H      oil                                       __________________________________________________________________________      .sup.a Prepared in Example 1F,F'.                                              .sup.b (CH.sub.2).sub. 5                                                       .sup.c C.sub.2 H.sub.5 OC(O)-                                                  .sup.d 3-N(CH.sub.3)COCH.sub.3                                           

                                      TABLE I-G                                    __________________________________________________________________________      ##STR95##                                                                     Comp.                                                                          No. R.sup.60                                                                            R.sup.61                                                                          R.sup.62                                                                          R.sup.63                                                                          R.sup.64                                                                          R.sup.65                                                                            R.sup.66                                                                               m.p. °C.                              __________________________________________________________________________     1G  NO.sub.2                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    H       112-117°                              2G.sup.a)                                                                          NO.sub.2                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-Cl    76-82°                                3G  Cl   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SO.sub.2 CH.sub.3                                                                    176-179°                              4G  CH.sub.3                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SO.sub.2 C.sub.2 H.sub.5                                                             gum                                          5G  CF.sub.3                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-CF.sub.3                                                                             viscous oil                                  6G  NO.sub. 2                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SO.sub.2 CH.sub.2 Cl                                                                 oil                                          7G  Cl   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-F     gum                                          8G  Cl   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          3-OC.sub.2 H.sub.5                                                                  4-SO.sub.2 C.sub.2 H.sub.5                                                             gum                                          9G  NO.sub.2                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SO.sub.2 CH.sub.3                                                                    gum                                          10G Cl   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SCH.sub.3                                                                            gum                                          11G CH.sub.3                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          3-NO.sub.2                                                                          H       gum                                          12G I    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    H       gum                                          13G OCH.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-Cl    gum                                          14G Cl   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          3-OCH.sub.3                                                                         4-Br    gum                                          15G NO.sub.2                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SO.sub.2 nC.sub.3 H.sub.7                                                            gum                                          16G NO.sub.2                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SO.sub.2 N(CH.sub.3).sub.2                                                           gum                                          17G NO.sub.2                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-CN    148-150°                              18G SO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    H       gum                                          19G NO.sub.2                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-CF.sub.3                                                                             gum                                          20G H    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-Cl    gum                                          21G H    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SCF.sub.3                                                                            gum                                          22G H    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-OCF.sub.3                                                                            gum                                          23G Cl   CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          3-Cl 4-SO.sub.2 C.sub.2 H.sub.5                                                             gum                                          24G H    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-C(O)CH.sub.3                                                                         gum                                          25G H    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SO.sub.2CH.sub.3                                                                     129-131°                              26G H    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SCH.sub.3                                                                            89-92°                                27G H    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-CF.sub.3                                                                             115-125°                              28G H    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-CN    87-95°                                __________________________________________________________________________      (a) prepared in Example 1G,G'.                                           

Herbicidal Screening Tests

As previously mentioned, the herein described compounds produced in the above-described manner are phytotoxic compounds which are useful and valuable in controlling various plant species. Selected compounds of this invention were tested as herbicides in the following manner.

Pre-emergence herbicide test.

On the day preceding treatment, seeds of eight different weed species are planted in loamy sand soil in individual rows using one species per row across the width of a flat. The seeds used are green foxtail (FT) (Setaria viridis), watergrass (WG) (Echinochloa crusgalli), wild oat (WO) (Avena fatua), annual morningglory (AMG) (Ipomoea lacunosa), velvetleaf (VL) (Abutilon theophrasti), Indian mustard (MD) (Brassica juncea), redroot pigweed (PW) (Amaranthus retroflexus) or curly dock (CD) (Rumex crispus), and yellow nutsedge (YNG) (Cyperus esculentus). Ample seeds are planted to give about 20 to 40 seedlings per row, after emergence, depending upon the size of the plants.

Using an analytical balance, 600 milligrams (mg) of the compound to be tested are weighed out on a piece of glassine weighing paper. The paper and compound are placed in a 60 milliliter (ml) wide-mouth clear bottle and dissolved in 45 ml of acetone or substituted solvent. Eighteen ml of this solution are transferred to a 60 ml wide-mouth clear bottle and diluted with 22 ml of a water and acetone mixture (19:1) containing enough polyoxyethylene sorbitan monolaurate emulsifier to give a final solution of 0.5% (v/v). The solution is then sprayed on a seeded flat on a linear spray table calibrated to deliver 80 gallons per acre (748 L/ha). The application rate is 4 lb/acre (4.48 Kg/ha).

After treatment, the flats are placed in the greenhouse at a temperature of 70°to 80° F. and watered by sprinkling. Two weeks after treatment, the degree of injury or control is determined by comparison with untreated check plants of the same age. The injury rating from 0 to 100% is recorded for each species as percent control with 0% representing no injury and 100% representing complete control.

The results of the tests are shown in the following Tables.

                  TABLE II-A                                                       ______________________________________                                         Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cm-                                                                            pd.                                                                            No.  FT     WG     WO   AMG   VL   MD   PW   CD   YNS                          ______________________________________                                         1A   100    90     20   40    65   50   35        80                           2A   80     90     0    30    80   90   20        90                           3A   0      0      0    40    40   40   0         0                            4A   100    100    50   35    100  100  90        95                           5A   100    95     65   35    90   85   50        95                           6A   50     25     0    25    100  100  35        80                           7A   80     90     10   60    100  100  100       80                           8A   95     95     45   40    100  80   95        95                           9A   95     100    55   30    100  90   100       95                           10A  100    100    60   20    85   100  100       95                           11A  85     100    30   40    100  100  100       95                           12A  85     85     90   75    80   95   90        90                           13A  85     75     10   10    85   65   95        90                           14A  40     10     80   0     65   40   65        100                          15A  40     60     20   30    100  30   75        95                           16A  80     80     20   55    75   90   40        95                           17A  20     --     10   25    100  95   85        90                           18A  65     --     30   70    100  100  85        90                           19A  45     60     0    30    40   0    20        60                           20A  30     85     20   40    95   85   40        45                           21A  80     100    0    80    100  100  95        95                           22A  20     10     0    20    75   30   45        10                           23A  45     95     10   0     100  85   100       95                           24A  --     100    0    25    70   90   --        100                          25A  --     100    25   80    100  100  --        100                          26A  40     15     0    0     0    10        0    30                           27A  40     80     10   20    60   50        30   75                           28A  65     75     0    65    100  95        75   55                           29A  100    95     55   10    80   75        85   95                           30A  20     20     20   10    40   40        50   20                           31A  75     95     20   20    100  95        75   10                           32A  90     85     20   0     100  85        75   30                           33A  80     70     0    40    20   40        90   80                           34A  60     40     0    20    95   100       100  60                           35A  0      10     0    0     10   20        20   10                           36A  0      0      0    20    100  100       100  0                            37A  40     0      0    20    100  60        90   --                           38A  10     40     0    20    90   80        20   20                           39A  80     10     0    0     0    0         0    90                           40A  60     0      0    0     0    0         0    90                           41A  100    100    85   40    95   100       100  100                          42A  60     100    25   0     0    0         0    25                           43A  100    100    45   40    80   90        90   100                          44A  90     100    0    60    100  100       100  95                           45A  100    100    0    60    100  100       100  100                          46A  20     60     0    100   100  100       100  20                           47A  60     70     20   100   100  100       100  60                           48A  60     0      0    0     0    0         0    40                           49A  100    100    50   10    60   20        90   100                          50A  100    100    80   10    60   60        90   100                          51A  100    100    90   100   100  100       85   100                          52A  100    100    60   10    100  100       60   100                          53A  0      20     0    0     20   20        0    10                           54A  10     45     10   0     0    0         0    40                           55A  90     100    60   100   100  100       90   100                          56A  40     70     40   40    40   60        70   50                           57A  100    100    90   100   100  100       85   100                          58A  90     95     0    20    20   40        40   100                          59A  95     100    85   75    100  100       90   98                           60A  95     100    50   50    100  100       90   98                           61A  100    100    75   100   100  100       95   95                           62A  100    100    95   75    100  100       100  80                           63A  100    100    40   65    100  100       100  95                           64A  100    100    98   100   100  100       100  90                           65A  100    100    80   100   100  100       100  90                           66A  100    100    75   100   100  100       100  98                           73A  100    100    60   80    100  100       75   90                           74A  100    100    70   80    100  100       80   100                          75A  70     100    0    50    100  100       100  80                           76A  40     90     25   10    100  100       100  10                           77A  100    100    90   100   100  100       85   --                           78A  100    100    80   100   100  100       90   --                           79A  50     100    50   50    95   100       100  60                           80A  0      0      0    0     0    0         0    0                            81A  100    100    50   15    100  100       90   100                          84A  100    100    85   0     0    100       20   100                          88A  60     95     35   95    100  100       95   80                           89A  75     100    40   100   100  100       95   60                           90A  100    100    90   100   100  100       100  85                           105A 80     95     25   0     95   50        70   50                           117A 95     100    0    25    100  100       50   95                           118A 100    100    60   100   100  100       100  85                           121A 95     100    50   75    100  95        100  80                           125A 100    100    50   80    100  100       100  85                           126A 70     100    80   80    100  100       100  80                           127A 100    100    100  100   100  100       --   80                           128A 100    100    100  100   100  100       --   80                           129A 100    100    95   90    100  100       --   80                           131A 70     85     0    20    95   98        95   90                           132A 100    100    95   90    100  100       --   80                           133A 100    100    100  100   100  100       --   80                           135A 100    100    100  80    100  100       --   80                           ______________________________________                                    

                  TABLE II-B                                                       ______________________________________                                         Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG      WO   AMG   VL   MD    CD   YNS                            ______________________________________                                         1B    0      85      10   75    100  80    80   75                             2B    90     100     65   100   100  100   100  100                            4B    100    100     80   60    100  80    90   100                            5B    80     100     20   40    100  100   80   100                            6B    40     100     0    40    100  100   80   100                            7B    100    10      100  80    100  100   90   100                            8B    100    100     60   45    60   60    80   100                            9B    60     100     40   20    60   60    60   100                            10B   100    100     40   5     80   60    80   100                            11B   100    100     90   10    20   20    40   100                            12B   0      20      0    0     10   20    10   0                              13B   100    100     90   40    100  100   100  100                            15B   90     90      50   20    --   100   100  80                             16B   100    100     95   100   100  100   90   100                            17B   100    100     100  100   100  100   100  97                             18B   100    100     85   100   100  100   90   95                             19B   100    100     95   100   100  100   100  95                             20B   100    100     85   100   100  100   100  90                             21B   100    100     100  100   100  100   100  95                             22B   100    100     80   100   100  100   100  90                             25B   100    100     75   80    100  100   100  90                             26B   100    100     65   30    100  100   100  90                             27B   20     95      60   5     100  100   90   100                            28B   100    100     80   20    90   40    80   100                            29B   100    100     70   20    100  100   100  100                            30B   100    100     80   60    100  100   80   100                            31B   80     100     40   10    60   60    80   100                            32B   20     40      0    --    60   100   60                                  33B   0      10      0    0     10   10    0    0                              34B   100    100     90   80    100  100   90   100                            35B   100    100     90   40    90   90    90   90                             36B   100    100     85   0     95   85    95   90                             37B   90     90      50   20    --   100   100  80                             39B   15     100     0    50    100  80    70   40                             40B   0      10      0    0     10   10    0    0                              41B   0      20      0    0     10   20    10   0                              42B   100    100     90   45    100  100   65   100                            43B   100    100     90   100   100  100   100  90                             44B   100    100     85   100   100  100   100  95                             45B   65     100     0    0     100  20    20   90                             46B   100    100     0    20    100  100   98   85                             47B   100    100     90   85    100  100   100  95                             48B   100    100     85   15    100  100   85   95                             49B   100    100     65   0     100  100   50   50                             50B   80     80      55   0     98   55    80   65                             51B   95     95      10   0     65   0     25   60                             52B   100    100     100  100   100  100   100  50                             53B   100    100     75   100   100  100   100  50                             54B   100    100     60   15    100  100   100  80                             55B   100    100     55   15    100  100   90   95                             56B   100    100     60   20    95   100   90   10                             57B   5      10      0    0     40   20    0    0                              58B   10     40      10   10    95   40    100  80                             59B   100    100     75   80    100  100   100  75                             60B   100    100     90   100   100  100   85   --                             61B   100    100     80   100   100  100   100  --                             62B   95     100     50   95    100  100   85   --                             63B   100    100     70   100   90   100   100  --                             64B   100    100     75   100   100  100   85   --                             65B   100    100     55   40    100  100   90   70                             66B   100    100     65   35    100  100   100  95                             67B   100    100     30   15    100  100   95   90                             71B   100    100     80   100   100  100   80   --                             72B   100    100     40   100   100  100   90   75                             73B   90     100     40   100   100  100   95   50                             74B   100    100     85   95    100  100   90   80                             75B   100    100     100  70    100  100   100  95                             77B   100    100     55   40    100  100   90   70                             81B   90     95      60   10    25   75    90   0                              82B   40     90      20   35    100  --    75   20                             91B   100    100     85   100   100  100   80   90                             101B  85     90      0    0     95   50    50   75                             ______________________________________                                    

                  TABLE II-C                                                       ______________________________________                                         Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG      WO   AMG   VL   MD    CD   YNS                            ______________________________________                                         1C    65     80      65   55    90   90    35   0                              ______________________________________                                    

                  TABLE II-D                                                       ______________________________________                                         Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG      WO   AMG   VL   MD    CD   YNS                            ______________________________________                                         1D    100    100     85   30    100  100   90   90                             2D    100    100     100  50    100  100   95   95                             3D    100    100     85   25    100  100   100  95                             4D    100    100     100  20    100  85    95   90                             5D    100    100     45   25    100  100   90   90                             6D    100    100     95   40    100  100   85   90                             9D    100    100     90   90    100  100   80   90                             10D   100    90      20   10    100  70    100  90                             11D   90     100     50   230   100  100   90   90                             12D   100    100     95   80    100  100   90   90                             13D   40     75      0    10    80   100   100  90                             14D   50     0       0    0     100  80    70   90                             15D   65     95      20   15    100  80    90   85                             17D   100    100     60   30    100  100   90   35                             18D   100    100     100  100   100  100   100  95                             19D   100    100     0    50    100  100   100  95                             20D   75     100     0    25    100  90    65   90                             21D   100    100     100  80    100  100   90   95                             22D   100    100     100  80    100  100   95   95                             23D   100    100     98   95    100  100   100  95                             25D   100    100     80   100   100  100   80   --                             26D   100    100     75   100   100  100   80   --                             27D   90     100     50   100   100  100   100  90                             28D   75     50      50   0     100  100   90   65                             30D   100    100     85   100   100  100   95   90                             31D   85     75      0    25    100  25    0    35                             32D   83     85      35   20    95   100   75   50                             36D   100    100     50   100   100  100   100  75                             37D   20     75      0    20    100  95    100  75                             38D   85     95      40   60    100  100   75   85                             39D   85     95      45   75    100  95    70   90                             51D   60     60      35   0     25   0     0    30                             52D   75     75      0    50    90   75    40   0                              65D   100    100     80   100   100  100   --   80                             ______________________________________                                          A blank (--) indicates that the weed was not tested.                     

                  TABLE II-E                                                       ______________________________________                                         Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG      WO   AMG   VL   MD    CD   YNS                            ______________________________________                                         1E    0      0       0    0     0    0     0    20                             2E    25     30      30   0     70   0     40   30                             3E    25     20      0    0     0    0     0    0                              4E    100    100     90   60    100  100   100  90                             5E    50     60      40   50    50   60    90   50                             6E    100    95      50   40    40   60    99   70                             16E   80     100     50   60    100  90    90   90                             20E   100    100     30   15    100  100   90   85                             21E   100    100     --   30    100  95    100  80                             ______________________________________                                          A blank (--) indicates that the weed was not tested.                     

                  TABLE II-F                                                       ______________________________________                                         Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG      WO   AMG   VL   MD    CD   YNS                            ______________________________________                                         1F    40     20      0    0     0    0     0    100                            2F    60     70      0    0     0    0     90   100                            3F    100    100     50   50    100  100   85   90                             4F    100    100     90   30    100  85    95   95                             5F    100    100     80   10    100  100   100  95                             6F    20     35      25   15    90   85    40   85                             7F    100    100     90   100   100  100   100  95                             8F    100    100     90   100   100  100   100  95                             9F    100    100     0    0     100  80    100  90                             10F   100    100     100  100   100  100   100  95                             11F   100    100     70   100   100  100   97   95                             12F   100    100     60   100   100  100   100  95                             13F   100    100     60   100   100  100   100  95                             14F   80     100     50   80    100  100   90   90                             15F   100    100     80   100   100  100   100  --                             16F   50     75      0    25    100  100   95   60                             17F   100    100     40   100   100  100   100  85                             18F   100    100     0    20    100  100   80   70                             20F   70     75      0    25    100  95    100  60                             21F   50     60      0    0     100  80    80   60                             22F   100    95      35   25    100  100   90   50                             23F   95     100     40   20    100  100   90   50                             24F   100    100     90   0     45   85    80   90                             25F   100    100     25   60    100  100   100  75                             34F   35     40      10   0     60   25    0    70                             37F   50     60      0    0     60   0     50   0                              38F   35     40      0    0     0    0     0    0                              52F   85     100     30   95    100  100   --   80                             53F   100    100     0    85    100  100   --   80                             54F   100    100     90   25    100  100   --   80                             ______________________________________                                          A blank (--) indicates that the weed was not tested.                     

                  TABLE II-G                                                       ______________________________________                                         Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT      WG      WO   AMG    VL   MD    YNS                               ______________________________________                                         1G    100     100     90   100    100  100   80                                2G    100     100     90   100    100  100   80                                3G    100     100     90   100    100  100   80                                4G    100     100     90   100    100  100   80                                5G    100     100     90   100    100  100   80                                6G*   100     100     100  100    100  --    20                                7G    100     100     80   100    100  100   80                                8G    85      100     80   100    100  100   80                                9G    100     100     80   100    100  100   80                                10G   100     100     80   100    100  100   80                                11G   100     100     80   100    100  100   80                                12G   100     100     80   90     100  100   0                                 13G   100     100     70   100    100  100   0                                 14G   100     100     75   100    100  100   90                                15G   100     100     80   100    100  100   90                                16G   100     100     90   100    100  100   80                                17G   100     100     80   100    100  100   80                                18G   100     100     90   85     100  100   80                                19G   100     100     100  100    100  100   80                                20G   70      95      10   100    100  100   0                                 21G   100     100     100  100    100  100   80                                22G   100     100     90   100    100  100   80                                23G   100     100     100  100    100  100   80                                24G   0       80      0    25     80   70    0                                 25G   100     100     80   100    100  100   80                                26G   100     100     100  80     100  100   80                                27G   100     100     100  100    100  100   80                                28G   100     100     90   100    100  100   80                                ______________________________________                                          A blank (--) indicates that the weed was not tested.                           * = Tested at 0.56 kg/ha.                                                

Post-Emergence Herbicide Test

This test is conducted in an identical manner to the testing procedure for the pre-emergence herbicide test, except the seeds of the eight different weed species are planted 10-12 days before treatment. Also, watering of the treated flats is confined to the soil surface and not to the foliage of the sprouted plants.

The results of the post-emergence herbicide test are reported in Table III.

                                      TABLE III-A                                  __________________________________________________________________________     Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.  FT  WG  WO  AMG  VL  MD  PW  CD  YNS                                      __________________________________________________________________________     1A   60  70  20  40   60  60  35      60                                       2A   30  70  0   50   90  85  30      80                                       3A   0   30  0   70   100 90  55      70                                       4A   95  98  20  98   100 100 30      95                                       5A   80  80  75  50   60  80  0       95                                       6A   40  40  10  60   100 100 75      65                                       7A   60  75  40  60   100 75  100     75                                       8A   85  80  75  70   95  80  90      90                                       9A   85  80  75  70   95  80  90      90                                       10A  95  85  90  60   95  95  80      95                                       11A  50  80  35  55   100 100 95      80                                       12A  45  75  50  55   75  60  50      80                                       13A  30  60  20  60   80  50  60      70                                       14A  20  10  20  50   45  40  40      0                                        15A  65  95  0   65   95  30  100     80                                       16A  65  80  20  85   85  30  30      80                                       17A  75  80  30  70   100 100 85      90                                       18A  100 95  10  100  100 100 100     90                                       19A  60  80  40  70   100 75  80      90                                       20A  65  80  10  85   95  95  100     70                                       21A  30  55  0   80   100 80  65      80                                       22A  0   30  0   20   45  0   30      20                                       23A  85  90  40  85   100 95  100     90                                       24A  0   80  0   70   90  74  --      100                                      25A  100 100 75  90   100 100 --      100                                      26A  45  30  0   40   70  65      0   45                                       27A  75  80  30  65   50  45      85  85                                       28A  75  60  60  75   100 70      80  25                                       29A  85  85  85  75   85  65      65  85                                       30A  75  50  20  10   0   0       20  40                                       31A  60  60  20  40   40  70      100 40                                       32A  60  25  20  40   90  65      20  40                                       33A  10  0   0   10   10  10      100 40                                       34A  10  10  0   5    50  30      80  0                                        35A  0   0   0   10   60  30      40  0                                        36A  0   0   0   20   20  20      0   0                                        37A  0   0   0   30   40  20      80  0                                        38A  10  10  10  20   10  20      20  10                                       39A  40  40  20  0    0   0       5   80                                       40A  90  70  40  20   60  80      20  65                                       41A  60  85  85  20   40  60      100 100                                      42A  60  50  40  70   20  40      60  60                                       43A  100 80  30  60   100 100     80  100                                      44A  80  85  0   60   90  90      100 80                                       45A  90  90  10  100  100 100     100 90                                       46A  80  100 0   60   100 100     100 100                                      47A  100 100 0   60   100 100     100 100                                      48A  40  40  20  10   10  10      90  40                                       49A  40  40  40  80   100 100     60  60                                       50A  80  60  60  50   50  60      80  70                                       51A  80  80  80  95   100 100     100 90                                       52A  60  60  20  20   40  40      90  60                                       53A  10  20  20  0    0   0       0   20                                       54A  20  40  20  5    0   0       0   40                                       55A  40  40  40  60   60  60      80  90                                       56A  100 100 75  80   100 100     100 90                                       57A  80  80  80  95   100 100     100 90                                       58A  60  70  10  70   10  10      20  80                                       59A  100 100 90  100  --  100     100 50                                       60A  100 100 100 100  --  100     100 70                                       61A  90  85  90  85   --  100     100 80                                       62A  100 85  100 75   100 100     100 35                                       63A  70  80  20  100  100 100     35  40                                       64A  75  75  90  70   90  70      40  40                                       65A  100 70  100 55   90  95      100 40                                       66A  100 75  100 90   95  95      100 20                                       73A  100 100 95  100  100 100     55  30                                       74A  100 95  75  100  100 100     85  40                                       75A  100 100 30  95   80  100     80  40                                       76A  80  80  75  75   100 95      95  25                                       77A  80  80  80  90   90  80      90  80                                       78A  80  85  75  85   80  95      100 50                                       79A  50  65  35  90   100 100     90  --                                       80A  40  40  10  20   60  0       0   30                                       81A  90  70  60  40   60  60      90  70                                       84A  100 100 100 20   40  40      80  60                                       88A  100 95  90  100  85  100     100 50                                       89A  100 100 75  85   75  85      95  50                                       90A  100 85  90  90   85  90      100 55                                       91A  100 100 100 100  95  100     95  60                                       105A 35  50  --  35   100 80      60  30                                       117A 40  60  0   25   50  50      80  --                                       118A 95  85  85  100  100 90      80  80                                       121A 65  85  40  100  100 100     60  50                                       125A 90  95  75  70   100 90      100 60                                       126A 40  50  20  40   60  50      100 80                                       127A 100 95  100 95   100 100         80                                       128A 85  95  80  60   100 95          80                                       129A 65  90  60  60   100 98          70                                       130A 100 95  95  95   100 100         70                                       131A 0   20  0   0    30  75      10  0                                        132A 95  100 100 80   95  95          50                                       133A 80  95  90  60   85  85          60                                       135A 70  100 100 75   100 95          70                                       __________________________________________________________________________

                  TABLE III-B                                                      ______________________________________                                         Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT      WG     WO    AMG  VL    MD   CD   YNS                            ______________________________________                                         1B    85      95     20    95   100   100  95   95                             2B    90      90     80    100  90    90   --   80                             4B    60      60     90    40   60    60   90   70                             5B    40      60     10    20   40    40   90   80                             6B    40      50     10    60   20    20   60   50                             7B    80      80     80    60   60    90   6    60                             8B    100     80     60    30   80    80   80   80                             9B    70      70     60    40   60    60   80   70                             10B   40      40     60    30   60    60   90   60                             11B   80      90     60    45   90    90   100  80                             12B   25      45     10    20   20    20   60   45                             13B   100     100    95    70   60    60   80   60                             15B   100     60     50    80   90    90   40   60                             16B   60      60     80    80   90    90   60   65                             17B   100     70     90    100  --    90   98   70                             18B   100     85     100   85   --    100  100  65                             19B   100     80     85    100  100   90   100  70                             20B   90      65     90    85   70    60   100  40                             21B   40      40     10    0    0     0    0    0                              22B   40      70     80    90   90    100  95   40                             25B   40      70     40    40   40    60   70   50                             26B   65      70     80    40   90    80   70   80                             27B   100     80     60    20   90    90   80   45                             28B   90      60     60    60   60    60   40   70                             29B   90      70     70    40   70    70   60   60                             30B   100     90     70    50   100   100  80   80                             31B   40      50     20    10   20    20   0    40                             32B   25      40     40    90   100   100  40   40                             33B   20      40     10    60   90    90   60   40                             34B   90      80     80    80   100   100  80   50                             35B   60      50     50    20   60    60   80   60                             36B   100     80     80    75   --    100  100  45                             37B   100     60     50    80   90    90   40   60                             39B   90      80     25    30   30    45   50   30                             40B   20      40     10    60   90    90   60   40                             41B   25      45     10    20   20    20   60   45                             42B   90      80     80    80   100   100  100  70                             43B   80      90     95    97   100   100  100  50                             44B   100     95     95    95   40    100  100  30                             45B   30      65     0     30   45    40   65   50                             46B   70      75     0     65   100   100  50   70                             47B   100     100    100   90   100   100  100  85                             48B   100     65     80    50   100   100  60   60                             49B   60      70     70    40   80    70   30   50                             50B   0       60     40    60   100   90   20   30                             51B   100     75     80    40   100   50   20   30                             52B   90      100    100   100  100   100  100  40                             53B   60      70     70    70   90    65   40   60                             54B   100     100    85    100  100   100  100  60                             55B   95      85     90    100  100   100  90   45                             56B   85      100    0     10   15    95   40   50                             57B   85      70     65    0    0     0    0    35                             58B   20      40     10    15   70    40   35   40                             59B   100     95     100   95   100   95   100  40                             60B   65      75     75    80   90    85   80   60                             61B   80      80     70    95   80    85   80   50                             62B   100     80     25    80   75    80   85   35                             63B   100     100    40    95   95    100  95   50                             64B   75      70     50    90   90    100  90   50                             65B   100     80     80    60   85    60   0    --                             66B   98      90     60    35   --    100  60   90                             67B   70      65     20    15   95    40   70   45                             71B   95      50     50    80   80    80   65   50                             72B   100     85     75    75   65    85   70   60                             73B   100     95     95    85   75    85   95   40                             74B   100     85     95    90   80    95   65   50                             75B   100     80     80    30   50    60   100  40                             81B   50      80     35    70   70    90   80   10                             82B   25      60     50    35   50    90   50   25                             91B   80      60     40    60   75    90   60   75                             101B  10      35     --    30   75    70   40   50                             ______________________________________                                          (--) = Specie did not germinate for some reason.                         

                  TABLE III-C                                                      ______________________________________                                         Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT      WG     WO    AMG  VL    MD   CD   YNS                            ______________________________________                                         1C    98      95     70    60   100   55   100  90                             ______________________________________                                    

                  TABLE III-D                                                      ______________________________________                                         Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT      WG     WO    AMG  VL    MD   CD   YNS                            ______________________________________                                         1D    95      75     85    70   100   90   85   40                             2D    45      70     95    75   100   90   100  65                             3D    100     80     100   90   --    100  100  80                             4D    100     80     100   100  --    100  85   75                             5D    90      70     45    60   95    70   60   80                             6D    95      75     80    70   100   90   90   65                             9D    100     90     90    100  100   100  95   85                             10D   45      75     10    15   100   100  20   75                             11D   100     70     60    75   100   100  100  45                             12D   100     75     100   100  100   100  90   90                             13D   30      55     0     30   60    60   15   60                             14D   20      65     0     40   70    60   40   25                             15D   20      75     30    20   100   70   60   40                             17D   85      80     50    65   95    95   100  60                             18D   100     95     100   100  100   100  100  75                             19D   20      95     30    100  100   35   30   70                             20D   30      80     15    100  100   45   20   70                             21D   100     80     100   55   100   90   100  80                             22D   100     80     100   60   100   95   95   95                             23D   100     90     90    100  100   100  85   70                             25D   70      75     50    85   90    85   60   75                             26D   100     85     85    95   95    95   90   60                             27D   90      90     60    100  100   100  100  --                             28D   15      45     20    50   75    80   15   30                             30D   100     100    80    85   85    85   100  --                             31D   80      90     100   100  100   100  100  60                             32D   75      85     85    75   75    90   95   50                             36D   35      50     35    70   50    50   35   60                             37D   60      75     15    70   70    90   90   40                             38D   95      90     65    70   90    90   100  50                             39D   95      85     30    50   70    80   100  50                             51D   60      75     60    35   30    60   40   60                             52D   60      75     25    100  100   100  100  75                             65D   70      50     70    90   80    85   --   80                             ______________________________________                                          A blank (--) indicates the weed was not tested.                          

                  TABLE III-E                                                      ______________________________________                                         Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG      WO   AMG   VL   MD   CD   YNG                             ______________________________________                                         1E    20     20      10   20    40   40   20   40                              2E    0      60      60   50    70   30   0    15                              3E    20     20      0    10    0    20   0    20                              4E    85     90      100  45    75   30   80   65                              5E    55     50      60   50    75   85   65   --                              6E    70     70      50   60    80   70   90   --                              16E   95     95      40   100   100  100  100  90                              20E   95     75      35   40    95   75   35   80                              21E   80     70      30   45    80   90   50   70                              ______________________________________                                          A blank (--) indicates the weed was not tested.                          

                  TABLE III-F                                                      ______________________________________                                         Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG      WO   AMG   VL   MD   CD   YNG                             ______________________________________                                         1F    60     40      20   30    40   40   50   60                              2F    50     40      10   20    20   20   40   60                              3F    100    100     85   100   100  100  100  75                              4F    100    100     95   85    100  95   100  60                              5F    95     95      100  65    90   25   70   45                              6F    40     30      0    20    90   25   20   70                              7F    100    100     100  100   100  100  100  90                              8F    100    95      100  100   100  100  100  70                              9F    65     65      0    20    80   65   90   80                              10F   100    100     100  100   100  100  100  70                              11F   85     90      90   85    90   80   30   60                              12F   100    90      65   80    100  100  100  50                              13F   100    95      100  100   100  100  90   --                              14F   100    100     100  100   100  100  100  50                              15F   25     35      15   30    80   25   20   0                               16F   100    85      70   75    90   90   50   --                              17F   100    100     100  100   100  100  100  --                              18F   90     85      85   85    90   95   70   40                              20F   40     60      10   60    100  100  100  50                              21F   35     60      10   60    100  100  80   60                              22F   95     95      35   100   100  100  90   50                              23F   100    100     40   100   100  100  90   50                              24F   100    75      100  60    --   100  100  60                              25F   95     95      90   95    100  100  95   35                              34F   50     40      0    35    50   70   30   50                              37F   20     60      0    30    30   50   50   50                              38F   25     50      0    25    25   50   20   20                              52F   0      60      50   50    10   50   --   20                              53F   0      50      0    50    50   50   --   30                              54F   90     75      60   50    50   80   --   80                              ______________________________________                                          A blank (--) indicates the weed was not tested.                          

                  TABLE III-G                                                      ______________________________________                                         Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT      WG      WO    AMG   VL    MD   YNG                               ______________________________________                                         1G    100     95      90    90    100   100  80                                2G    100     100     100   100   100   100  80                                3G    100     100     95    100   100   100  90                                4G    100     100     100   100   100   100  90                                5G    100     100     100   100   100   100  100                               6G*   10      80      50    75    40    --   0                                 7G    70      75      70    90    90    80   80                                8G    50      80      70    90    90    80   30                                9G    70      80      70    90    90    80   30                                10G   75      80      70    80    60    50   70                                11G   70      80      70    80    80    80   80                                12G   100     75      90    75    80    80   80                                13G   60      70      70    100   100   100  80                                14G   20      70      40    60    80    80   70                                15G   90      70      70    75    80    90   70                                16G   50      70      80    60    80    90   70                                17G   90      60      70    65    80    80   80                                18G   30      50      80    95    95    80   70                                19G   100     100     95    90    100   100  80                                20G   10      40      5     70    80    90   70                                21G   95      90      95    95    100   100  70                                22G   80      90      90    80    100   100  70                                23G   90      80      80    80    90    80   30                                24G   0       30      0     40    80    20   0                                 25G   0       20      0     10    10    20   0                                 26G   80      70      70    80    80    80   70                                27G   90      90      90    80    80    90   60                                28G   70      65      50    80    80    80   70                                ______________________________________                                          A blank (--) indicates the weed was not tested.                                * = Tested at 0.56 kg/ha.                                                

Pre-Emergence Multi-Weed Herbicide Test

Several compounds were evaluated at an application rate of 2 lb/acre (2.24 kg/ha) or 1 lb/acre (1.12 kg/ha) for pre-emergence activity against a larger number of weed species.

The process was generally similar to the pre-emergence herbicide test described above except that only 300 or 150 milligrams of test compound were weighed out and the application rate was 40 gallons per acre.

Redroot pigweed (PW) and curly dock (CD) were eliminated in this test and the following weed species were added:

    ______________________________________                                         Grasses:                                                                              downy brome    Bromus tectorum                                                                              (DB)                                              annual ryegrass                                                                               Lolium multiflorum                                                                           (ARG)                                             rox-orange sorghum                                                                            Sorghum bicolor                                                                              (SHC)                                             hemp sesbania  Sesbania exaltata                                                                            (SESB)                                            nightshade     Solanum sp.   (SP)                                              cocklebur      Xattiium sp.  (CB)                                       ______________________________________                                    

The results of the 2.24 kg/ha test are shown in Table IV and the results of the 1.12 kg/ha test are shown in Table VI.

Post-Emergence Multi-Weed Herbicide Test

Several compounds were evalated at an application rate of 2 lb/acre (2.24 kg/ha) or 1 lb/acre (1.12 kg/ha) for post-emergence activity against the larger number of weed species that are used in the pre-emergent multi-herbicide test.

The process was generally similar to the post-emergence herbicide test described above except that only 300 or 150 milligrams of test compound were weighed out and the application rate was 40 gallons per acre.

The results of the 2.24 kg/ha test are shown in Table V and the results for the 1.12 kg/ha test are shown in Table VII.

                                      TABLE IV-A                                   __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 2.24 kg/ha                                                  Cmpd.                                                                          No. DB  FT  ARG WG  SHC WO  BSG AMG SESB                                                                               VL  SP   MD  YNS   CB                  __________________________________________________________________________     67A 20  90  25  98  80  60  90  45  90  45  20   85    85  15                  68A 65  98  98  100 100 60  95  100 100 100 80   100   95  100                 69A 65  100 70  100 100 65  95  100 95  70  65   100   90  --                  70A 98  100 100 100 100 90  98  90  100 90  60   100   95  80                  71A 60  20  100 100 100 80  95  35  40  100 20   90    100 40                  72A 100 100 100 100 100 100 100 100 90  100 60   100   100 20                  83A 15  45  25  90  15  5   90  45  35  20  0    20    75  --                  86A 20  0   15  60  60  20  70  25  45  100 20   100   15  35                  87A 100 90  85  100 85  25  30  35  85  100 85   100   95  40                  __________________________________________________________________________

                                      TABLE VI-A                                   __________________________________________________________________________     Post-Emergence Multi-weed Herbicide Test                                       Application Rate - 2.24 hg/ha                                                  Cmpd.                                                                          No. DB  FT  ARG WG  SHC WO  BSG AMG SESB                                                                               VL  SP   MD  YNS   CB                  __________________________________________________________________________     86A 60  100 50  90  50  60  90  70  100 100 20   100 20    --                  87A 95  100 30  100 80  70  80  95  100 100 100  100 70    --                  __________________________________________________________________________

                                      TABLE V-A                                    __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB  FT  ARG WG  SHC WO  BSG AMG SESB                                                                               VL  SP   MD  YNS   CB                  __________________________________________________________________________     82A 35  100 85  100 65  60  90  50  90  60  30   97  90    40                  85A 100 100 100 100 100 85  100 20  10  100 65   100 100   30                  92A 15  20  45  100 90  40  80  95  95  100 25   100 90    40                  93A 30  75  40  100 100 60  90  100 100 100 35   100 90    40                  94A 30  70  40  100 100 30  65  95  85  100 0    100 90    30                  95A 0   0   0   85  60  15  70  65  60  100 80   90  10    20                  96A 95  100 98  100 100 70  100 100 95  90  80   100 95    --                  97A 100 100 98  100 100 100 100 100 95  100 70   100 95    100                 98A 10  0   0   0   20  25  70  0   20  0   0    80  30    --                  99A 15  0   0   75  25  0   20  30  60  15  20   30  25    0                   100A                                                                               0   0   0   0   0   0   20  10  0   0   0    15  0     --                  101A                                                                               100 98  95  100 100 70  98  100 100 100 20   100 95    --                  102A                                                                               25  20  35  100 100 45  95  70  100 100 60   100 90    --                  103A                                                                               80  60  45  100 100 40  90  65  90  100 0    100 95    0                   106A                                                                               100 100 60  40  95  35  100 35  90  100 70   100 90    --                  107A                                                                               100 100 100 100 100 90  100 100 100 100 80   100 95    30                  108A                                                                               100 100 100 100 100 85  100 100 100 100 30   100 95    100                 109A.sup.a                                                                         65  20  85  100 98  60  90  30  50  100 50   100 90    100                 110A                                                                               0   60  30  100 65  25  65  25  30  100 0    100 60    0                   111A                                                                               100 100 100 100 100 75  98  100 100 100 90   100 --    70                  112A                                                                               100 100 90  100 100 95  100 100 100 100 100  100 --    --                  113A                                                                               65  95  40  100 100 30  90  70  100 100 0    100 --    30                  114A                                                                               70  100 25  100 100 40  100 100 100 100 30   100 95    80                  115A                                                                               100 100 100 100 100 100 100 100 100 100 45   100 85    100                 116A                                                                               25  15  20  100 65  35  65  45  50  100 0    100 95    10                  119A                                                                               100 100 100 100 100 100 100 100 100 100 95   100 95    90                  120A                                                                               100 100 100 100 100 95  100 100 100 100 100  100 90    100                 122A                                                                               80  80  45  100 60  65  70  100 100 100 100  100 90    100                 123A                                                                               0   100 50  100 85  0   60  100 90  100 80   100 100   20                  124A                                                                               25  50  65  90  65  0   40  75  80  100 40   90  80    60                  __________________________________________________________________________      .sup.a = application rate was 0.56 kg/ha.                                

                                      TABLE VII-A                                  __________________________________________________________________________     Post-Emergence Multi-weed Herbicide Test                                       Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB  FT  ARG WG  SHC WO  BSG AMG SESB                                                                               VL  SP   MD  YNS   CB                  __________________________________________________________________________     82A 60  40  10  98  35  10  30  70  100 100 100  90  45    --                  85A 60  60  35  100 45  60  85  50  100 100 100  100 60    --                  92A 70  55  20  80  80  45  100 95  90  80  20   95  70    90                  93A 90  90  70  95  95  75  90  98  95  85  35   100 60    90                  94A 100 85  45  90  100 90  100 100 90  90  30   100 60    85                  95A 20  60  0   80  70  0   45  60  75  90  0    65  20    --                  96A 95  100 90  95  100 80  95  100 100 100 70   100 70    90                  97A 100 100 95  100 100 100 100 100 100 100 90   100 70    100                 98A 20  0   0   45  10  50  30  20  65  100 0    75  35    80                  99A 25  75  15  80  65  10  25  85  100 100 80   100 10    --                  100A                                                                               10  35  0   70  50  5   20  30  70  40  0    100 10    100                 101A                                                                               30  60  25  100 60  60  80  100 100 100 30   100 70    --                  103A                                                                               90  100 25  100 100 80  100 100 100 100 15   100 40    --                  104A                                                                               98  98  25  98  100 15  100 100 100 100 60   100 95    --                  106A                                                                               75  90  30  90  70  25  100 100 100 100 80   100 75    --                  107A                                                                               100 100 80  90  85  100 100 100 100 100 60   100 40    --                  108A                                                                               100 100 65  90  60  95  100 100 100 100 90   100 90    --                  109A.sup.a                                                                         90  60  45  90  70  60  98  95  95  100 98   80  55    --                  110A                                                                               50  50  20  100 50  10  40  100 98  98  20   100 35    45                  111A                                                                               85  90  80  90  70  60  95  100 90  100 65   100 80    60                  112A                                                                               100 100 90  100 100 95  100 100 100 100 45   100 95    70                  113A                                                                               70  50  20  90  60  50  80  95  95  100 60   100 --    60                  114A                                                                               85  100 15  100 100 60  00  100 100 100 100  100 60    --                  115A                                                                               100 100 45  100 100 80  100 100 100 100 100  100 90    --                  116A                                                                               80  60  25  90  35  40  45  75  90  100 40   90  75    60                  119A                                                                               60  70  30  95  70  20  90  100 100 100 90   100 30    85                  120A                                                                               75  90  60  95  80  45  100 100 90  100 65   100 35    100                 122A                                                                               60  90  15  100 30  15  15  100 100 100 75   100 45    95                  123A                                                                               0   100 35  100 50  15  85  100 100 100 100  100 70    85                  124A                                                                               25  100 35  40  35  0   40  95  100 100 100  100 85    75                  __________________________________________________________________________      A = Application rate was 0.56 kg/ha.                                           A dash mark (--) is used in Tables II-VII to indicate that no percent          control number was available.                                            

                                      TABLE IV-B                                   __________________________________________________________________________     Pre-Emergence Multi-Weed Herbicide Test                                        Applicaton Rate - 2.24 kg/ha                                                   Cmpd.                                                                          No. DB  FT  ARG WG  SHC WO  BSG AMG SESB                                                                               VL  SP   MD  YNS   CB                  __________________________________________________________________________     14B 80  100 100 100 100 80  95  70  60  100 40   85  100   10                  21B 85  100 90  100 100 85  100 100 100 100 70   100 95    100                 24B 100 100 100 100 100 100 100 100 100 100 75   100 95    --                  38B 100 100 100 100 100 100 100 20  10  100 20   95  100   20                  88B 75  100 60  100 100 70  60  20  40  100 0    100 60    20                  89B 20  60  30  85  95  55  40  15  20  65  0    100 35    50                  90B 60  100 60  100 100 45  30  100 100 100 15   100 50    85                  103B                                                                               95  100 75  100 100 50  85  100 100 100 80   100 80    40                  104B                                                                               60  100 60  100 100 45  30  100 100 100 15   100 50    85                  __________________________________________________________________________      (--) = Specie did not germinate for some reason.                         

                                      TABLE V-B                                    __________________________________________________________________________     Post-Emergence Multi-Weed Herbicide Test                                       Application Rate - 2.24 kg/ha                                                  Cmpd.                                                                          No. DB  FT  ARG WG  SHC WO  BSG AMG SESB                                                                               VL  SP   MD  YNS   CB                  __________________________________________________________________________     24B 35  25  45  60  65  85  90  100 100 --  90   100 65    --                  88B 60  30  30  90  100 80  100 100 100 100 30   100 20    100                 89B 50  70  35  90  60  35  20  100 90  100 35   100 15    100                 90B 30  100 40  100 70  10  25  100 100 100 30   90  50    95                  103B                                                                               95  100 70  100 65  75  65  100 100 100 65   100 50    100                 104B                                                                               30  100 40  100 70  10  25  100 100 100 30   90  50    95                  __________________________________________________________________________      (--) = Specie did not germinate for some reason.                         

                                      TABLE VI-B                                   __________________________________________________________________________     Pre-Emergence Multi-Weed Herbicide Test                                        Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB  FT  ARG WG  SHC                                                                               WO BSG AMG SESB                                                                               VL SP  MD  YNS CB                        __________________________________________________________________________     1B  25  10  30  85  55 0  --  55  --  100                                                                               --  75  75  35                        23B 55  95  90  100 95*                                                                               95 95  98  80  -- 10  100 95  --                        68B 65  100 60  100 100*                                                                              6  90  100 90  100                                                                               20  100 30  40                        69B 70  100 60  100 100*                                                                              95 95  100 95  100                                                                               0   100 85  25                        70B 60  100 75  100 100*                                                                              85 100 100 90  100                                                                               25  100 90  25                        76B 100 100 85  100 100*                                                                              85 98  100 95  -- 35  100 95  --                        78B 40  70  15  95  75*                                                                               25 80  65  75  -- 0   100 80  --                        79B 100 100 100 100 100                                                                               98 100 100 85  100                                                                               85  100 95  --                        80B 98  100 95  100 100                                                                               60 98  99  90  100                                                                               35  100 85  --                        83B 20  100 60  100 100*                                                                              40 90  85  65  100                                                                               0   100 85  --                        84B 0   90  25  98  100*                                                                              30 90  20  35  100                                                                               5   100 50  --                        85B 80  100 50  100 100                                                                               60 90  100 90  100                                                                               0   100 95  --                        86B 60  90  40  100 100                                                                               60 70  35  60  100                                                                               100 100 --  --                        87B 0   90  15  100 85 15 70  40  60  100                                                                               40  90  20  --                        92B 20  40  10  95  40 10 60  65  30  100                                                                               0   55  60  0                         93B 60  95  20  100 100                                                                               75 100 100 100 100                                                                               0   100 40  35                        94B 0   80  40  100 95 25 85  80  40  100                                                                               10  85  55  10                        95B 98  100 30  100 100                                                                               40 90  100 100 100                                                                               40  100 90  30                        96B 100 100 75  100 100                                                                               95 100 100 100 100                                                                               60  100 85  100                       97B 100 100 90  100 100                                                                               95 100 100 100 100                                                                               60  100 95  100                       98B 95  100 100 100 100                                                                               80 100 100 100 100                                                                               50  100 100 60                        99B**                                                                              --  100 75  100 100*                                                                              20 75  50  75   95                                                                               0   --  85  30                        100B                                                                               100 98  98  100 100                                                                               90 95  100 75  100                                                                               70  100 95  40                        102B                                                                               0   100 25  100 90 75 95  60  60  100                                                                               30  100 90  --                        __________________________________________________________________________      * = seedling johnsongrass (Sroghum halepense) was substituted for rox          organge sorghum.                                                               ** = Application rate was 0.56 kg/ha                                           (--) = Specie did not germinate for some reason.                         

                                      TABLE VII-B                                  __________________________________________________________________________     Post-Emergence Multi-Weed Herbicide Test                                       Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB  FT  ARG WG  SHC                                                                               WO BSG AMG SESB                                                                               VL SP  MD  YNS CB                        __________________________________________________________________________     1B  45  35  40  90  35 10 --  60  --  75 --  60  50  55                        23B 90  100 80  90  90*                                                                               90 90  80  90  90 40  70  25  --                        68B 50  60  40  85  80*                                                                               75 100 95  90  85 55  100 40  --                        69B 70  80  35  90  90*                                                                               80 90  80  85  90 20  90  25  --                        70B 100 90  80  100 100*                                                                              95 100 100 95  80 30  75  45  90                        76B 100 100 98  100 100*                                                                              100                                                                               100 100 100 100                                                                               60  100 40  --                        78B 100 90  80  85  100*                                                                              70 90  100 100 100                                                                               0   90  45  --                        79B 80  35  45  70  60*                                                                               70 70  45  98  100                                                                               35  90  20  --                        80B 60  70  25  90  60*                                                                               60 85  70  90  100                                                                               15  100 25  100                       85B 95  100 65  100 80 90 100 100 100 100                                                                               25  100 85  --                        86B 30  60  20  75  50 50 60  50  65  100                                                                               10  100 20  80                        87B 0   0   0   100 45 20 30  60  90  80 0   100 30  45                        92B 20  80  10  85  15  0 30  100 40  100                                                                               0   60  60  30                        93B 70  100 25  100 100                                                                               85 100 100 100 100                                                                               100 100 80  --                        94B 20  70  30  90  80 30 20  100 100 100                                                                               60  30  30  100                       95B 60  90  15  95  95 25 90  100 100 100                                                                               75  100 70  100                       96B 50  80  0   90  70 30 100 100 100 100                                                                               40  100 20  100                       97B 65  100 35  100 75 70 80  100 100 100                                                                               50  100 50  100                       98B 95  100 65  95  90 100                                                                               95  100 100 90 40  80  60  95                        99B**                                                                              --  100 95  90  90*                                                                               90 100 25  80  40 100 --  35  75                        100B                                                                               65  75  60  80  75 60 85  100 100 100                                                                               45  100 65  60                        102B                                                                               30  75  20  80  60  0 40  70  100 100                                                                               30  100 75  --                        __________________________________________________________________________      * = Seedling johnsongram (Sorghum halepense) was substituted for roxorang      sorghum.                                                                       ** = Application rate was 0.56 kg/ha.                                          (--) Specie did not germinate for some reason.                           

                                      TABLE IV-C                                   __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP                                                                               MD YNS                                                                               CB                                __________________________________________________________________________     2C  0  100                                                                               0   100                                                                               -- 45 70 65  50  100                                                                               15                                                                               100                                                                               90 --                                __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE V-C                                    __________________________________________________________________________     Post-Emergence Multi-Weed Herbicidal Activity                                  Application Rate -- 1.12 kg/ha                                                 Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     2D  0  30 0   100                                                                               -- 0  60  85 95  100                                                                               100                                                                               90 40 --                               __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE IV-D                                   __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 2.24 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     7D  100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               95 100                              8D  100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               95 --                               16D.sup.a                                                                          70 100                                                                               65  100                                                                               100                                                                               60 98 55  100 100                                                                               90 100                                                                               90 --                               24D 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               100                                                                               --                               29D 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               30 100                                                                               95 80                               33D 75 15 60  90 90 20 95 100 100 100                                                                               60 100                                                                               95 100                              53D 100                                                                               100                                                                               100 100                                                                               100                                                                               90 100                                                                               100 100 100                                                                               100                                                                               100                                                                               95 100                              57D 100                                                                               100                                                                               25  100                                                                               100                                                                               30 25 100 100 100                                                                               100                                                                               100                                                                               95 100                              64D.sup. a                                                                         -- 0  0   95 35 0  15 50  75  75 25 -- 75 40                               66D.sup.a                                                                          -- 0  15  15 50 20 50 100 100 75 0  -- 90 100                              67D.sup.a                                                                          -- 0  0   100                                                                               100                                                                               0  25 95  75  50 25 -- 30 75                               69D.sup.a                                                                          -- 30 0   100                                                                               100                                                                               0  70 100 100 100                                                                               35 -- 95 100                              70D.sup.a                                                                          -- 100                                                                               10  100                                                                               100                                                                               25 65 100 100 100                                                                               0  -- 95 100                              __________________________________________________________________________      (--) = Not tested.                                                             (a) = Tested at 0.28 kg/ha.                                              

                                      TABLE V-D                                    __________________________________________________________________________     Pre-Emergence Mu1ti-weed Herbicide Test                                        Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     34D 90 85 30  95 -- 45 98 75  100 100                                                                               40 100                                                                               50 --                               35D 100                                                                               85 70  100                                                                               -- 90 100                                                                               100 100 100                                                                               40 100                                                                               75 --                               40D 100                                                                               100                                                                               20  100                                                                               -- 70 100                                                                               98  98  100                                                                               20 100                                                                               50 --                               41D 100                                                                               100                                                                               80  100                                                                               -- 60 100                                                                               100 100 100                                                                               25 100                                                                               95 --                               42D 50 60 40  85 -- 30 100                                                                               100 100 100                                                                               100                                                                               100                                                                               90 --                               43D 90 95 60  100                                                                               -- 30 98 100 98  100                                                                               45 100                                                                               95 --                               44D 60 100                                                                               20  100                                                                               -- 60 100                                                                               100 90  100                                                                               20 100                                                                               80 --                               45D 95 100                                                                               35  100                                                                               -- 60 90 100 100 100                                                                               0  100                                                                               90 --                               46D 100                                                                               100                                                                               90  100                                                                               -- 95 100                                                                               100 100 100                                                                               40 100                                                                               95 --                               47D 100                                                                               100                                                                               100 100                                                                               -- 98 100                                                                               100 98  100                                                                               30 100                                                                               95 --                               48D 100                                                                               100                                                                               100 100                                                                               -- 100                                                                               100                                                                               100 100 100                                                                               90 100                                                                               100                                                                               --                               49D 100                                                                               100                                                                               100 100                                                                               -- 100                                                                               100                                                                               100 100 100                                                                               90 100                                                                               -- --                               50D 100                                                                               100                                                                               100 100                                                                               100                                                                               85 100                                                                               100 100 100                                                                               90 100                                                                               98 --                               54D 100                                                                               100                                                                               85  100                                                                               100                                                                               15 100                                                                               25  100 100                                                                               65 100                                                                               95 100                              55D 85 100                                                                               35  100                                                                               98 15 100                                                                               15  100 100                                                                               65 100                                                                               95 --                               56D 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               100                                                                               100                              58D 98 100                                                                               40  95 40 20 95 100 100 100                                                                               85 100                                                                               100                                                                               95                               59D 100                                                                               100                                                                               100 100                                                                               100                                                                               90 100                                                                               100 100 100                                                                               100                                                                               100                                                                               85 80                               60D 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               75 100                                                                               85 80                               __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE VI-D                                   __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 0.56 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     61D -- 100                                                                               65  100                                                                               65 20 80 20  40  80 10 -- 20 0                                62D -- 50 35  70 50 0  0  0   25  50 0  -- 0  0                                63D 100                                                                               100                                                                               100 100                                                                               100                                                                               95 100                                                                               90  95  100                                                                               75 100                                                                               100                                                                               85                               68D -- 0  20  0  0  0  0  60  100 100                                                                               90 -- 75 75                               71D -- 50 40  50 75 40 35 75  50  70 0  -- 75 75                               72D -- 35 60  100                                                                               85 50 100                                                                               25  65  100                                                                               35 -- 100                                                                               35                               73D -- 90 70  100                                                                               95 25 0  70  100 100                                                                               0  -- 50 25                               __________________________________________________________________________      (--) =  Not tested.                                                      

                                      TABLE VII-D                                  __________________________________________________________________________     Post-Emergence Multi-Weed Herbicidal Activity                                  Application Rate -- 2.24 kg/ha                                                 Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     7D  100                                                                               100                                                                               100 100                                                                               80 90 10 95  100 100                                                                               55 100                                                                               45 100                              16D.sup.a                                                                          100                                                                               85 35  100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               85 70                               24D 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               100                                                                               --                               29D 100                                                                               100                                                                               60  100                                                                               90 100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               100                                                                               --                               33D 90 98 85  100                                                                               100                                                                               80 100                                                                               100 100 100                                                                               90 100                                                                               90 100                              53D 100                                                                               100                                                                               60  100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               100                                                                               --                               57D 25 40 10  100                                                                               10 0  10 100 95  100                                                                               35 100                                                                               -- 100                              64D.sup.a                                                                          -- 0  0   90 0  0  85 40  100 80 50 -- 35 100                              66D.sup.a                                                                          -- 0  0   65 0  0  70 75  80  75 0  -- 25 75                               67D.sup.a                                                                          -- 0  0   75 35 0  40 70  80  60 0  -- 0  100                              69D.sup.a                                                                          -- 0  0   80 35 0  100                                                                               90  100 100                                                                               40 -- 35 100                              70D.sup.a                                                                          -- 100                                                                               0   100                                                                               70 90 90 100 100 100                                                                               30 -- 25 100                              __________________________________________________________________________      (--) = Not tested.                                                             (a) = Tested at 0.28 kg/ha.                                              

                                      TABLE VIII-D                                 __________________________________________________________________________     Post-Emergence Multi-weed Herbicide Test                                       Applicaton Rate - 1.12 kg/ha                                                   Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     34D 90 85 30  95 -- 45 98 75  100 100                                                                               40 100                                                                               50 --                               35D 100                                                                               85 70  100                                                                               -- 90 100                                                                               100 100 100                                                                               40 100                                                                               75 --                               40D 75 100                                                                               5   100                                                                               -- 50 75 100 100 100                                                                               40 100                                                                               30 --                               41D -- -- --  -- -- -- -- --  --  -- -- -- -- --                               42D 40 100                                                                               35  100                                                                               -- 50 80 100 100 100                                                                               80 100                                                                               70 --                               43D 60 70 20  100                                                                               -- 55 60 100 100 100                                                                               95 100                                                                               70 --                               44D -- -- --  -- -- -- -- --  --  -- -- -- -- --                               45D -- -- --  -- -- -- -- --  --  -- -- -- -- --                               46D -- -- --  -- -- -- -- --  --  -- -- -- -- --                               47D 90 100                                                                               35  100                                                                               -- 75 90 100 100 100                                                                               25 100                                                                               45 --                               48D 80 100                                                                               60  100                                                                               -- 60 80 100 100 100                                                                               85 100                                                                               60 --                               49D -- -- --  -- -- -- -- --  --  -- -- -- -- --                               50D 90 80 60  95 80 90 100                                                                               100 100 100                                                                               65 100                                                                               80 --                               54D 35 50 30  100                                                                               30 15 90 100 100 100                                                                               100                                                                               100                                                                               95 --                               55D 100                                                                               100                                                                               20  100                                                                               90 20 100                                                                               90  100 100                                                                               100                                                                               100                                                                               -- --                               56D 75 90 75  95 90 25 100                                                                               100 100 100                                                                               90 100                                                                               90 100                              58D 70 100                                                                               40  100                                                                               95 30 95 100 95  100                                                                               95 100                                                                               95 85                               59D 90 100                                                                               95  100                                                                               100                                                                               50 100                                                                               100 100 100                                                                               95 100                                                                               100                                                                               95                               60D 95 100                                                                               100 100                                                                               100                                                                               75 95 100 100 100                                                                               95 100                                                                               100                                                                               100                              __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE IX-D                                   __________________________________________________________________________     Post-Emergence Multi-weed Herbicide Test                                       Application Rate - 0.56 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     61D -- 40 0   50 35 0  40 75  95  100                                                                               0  -- 25 50                               62D -- 35 0   20 0  0  20 35  60  100                                                                               0  -- 0  100                              63D 100                                                                               100                                                                               85  98 85 100                                                                               100                                                                               100 100 100                                                                               100                                                                               85 85 95                               68D -- 30 40  85 0  25 60 80  95  100                                                                               95 -- 0  80                               71D -- 50 0   80 65 0  75 100 80  100                                                                               50 -- 25 100                              72D -- 90 70  80 50 50 75 85  100 100                                                                               90 -- 100                                                                               100                              73D -- 100                                                                               15  100                                                                               75 75 85 100 100 90 60 -- 80 100                              __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE IV-E                                   __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 2.24 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG JG WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                 __________________________________________________________________________     17E 95 85 35  100                                                                               85 25 90 100 100 100                                                                               40 100                                                                               95                                  18E 0  0  0   50 20 0  15 60  45  100                                                                               0  100                                                                               --                                  __________________________________________________________________________

                                      TABLE V-E                                    __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG JG WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                 __________________________________________________________________________     7E  30 70 20  100                                                                               75 0  90 100 95  100                                                                               100                                                                               100                                                                               90                                  8E  95 95 45  100                                                                               98 25 90 100 95  100                                                                               90 100                                                                               90                                  9E  10 70 40  100                                                                               20 0  80 100 85  100                                                                               40 100                                                                               95                                  10E 100                                                                               100                                                                               10  100                                                                               40 0  90 100 100 100                                                                               80 100                                                                               100                                 11E 90 100                                                                               90  100                                                                               100                                                                               65 100                                                                               100 90  100                                                                               30 100                                                                               65                                  12E 100                                                                               100                                                                               80  100                                                                               100                                                                               85 90 100 100 100                                                                               85 100                                                                               90                                  13E 0  100                                                                               10  100                                                                               100                                                                               80 70 80  90  100                                                                               70 100                                                                               80                                  15E 0  10 0   90 0  0  15 35  30  100                                                                               10 85 75                                  19E 100                                                                               90 0   100                                                                               20 10 40 95  100 100                                                                               100                                                                               100                                                                               65                                  __________________________________________________________________________

                                      TABLE VI-E                                   __________________________________________________________________________     Post-Emergence Multi-Weed Herbicidal Activity                                  Application Rate - 2.24 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG JG WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                 __________________________________________________________________________     17E 80 100                                                                               55  95 90 20 60 100 100 100                                                                               75 100                                                                               70                                  18E 0  100                                                                               0   98 20 0  10 70  60  100                                                                               10 100                                                                               45                                  __________________________________________________________________________

                                      TABLE VII-E                                  __________________________________________________________________________     Post-Emergence Multi-Weed Herbicidal Activity                                  Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT  ARG WG  JG  WO BSG AMG SESB                                                                               VL  SP  MD  YNS                          __________________________________________________________________________     7E  25 30  0   70  60  20 90  75  95  85  50  100 35                           8E  80 80  20  70  70  40 80  50  80  80  60  60  35                           9E  0  30  0   75  15  25 100 95  100 100 60  100 25                           10E 60 80  20  70  35  25 80  75  90  90  70  100 45                           11E 45 100 20  100 100 40 50  100 100 100 20  100 35                           12E 70 60  30  100 100 80 98  90  100 100 70  98  40                           13E 25 100 10  100 100 85 100 80  100 100 10  90  25                           15E 30 65  10  90  50  30 20  85  80  98  30  65  15                           19E 20 60  10  90  10  15 90  100 100 70  100 40  85                           __________________________________________________________________________

                                      TABLE IV-F                                   __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB  FT  ARG WG  JG  WO  BSG AMG SESB                                                                               VL SP  MD YNS                                                                               CB                        __________________________________________________________________________     19F 40  35  60  100 90  30  90  100 100 -- 20  100                                                                               90 --                        26F 25  70  45  95  60  25  85  35  75  -- 20  100                                                                               95 90                        27F 45  65  40  100 60  25  80  100 85  100                                                                               40  100                                                                               95 35                        28F 80  100 90  100 100 90  100 70  90  100                                                                               30  100                                                                               95 35                        29F 90  45  75  100 85  40  90  95  90  100                                                                               40  100                                                                               95 --                        30F 90  45  75  100 90  75  100 100 80  100                                                                               60  100                                                                               95 --                        31F 60  65  75  100 100 55  95  100 100 100                                                                               100 100                                                                               95 --                        32F 90  100 90  100 100 65  85  100 90  100                                                                               95  100                                                                               85 --                        33F 100 100 95  100 100 95  100 100 100 100                                                                               25  100                                                                               90 --                        35F 90  100 100 100 --  90  90  100 90  100                                                                               10  100                                                                               75 --                        36F 90  35  85  100 --  15  80  95  90  100                                                                               50  100                                                                               95 --                        39F 100 100 100 100 100 95  100 100 100 100                                                                               100 100                                                                               98 --                        40F 100 100 80  100 100 70  100 100 100 100                                                                               90  100                                                                               95 --                        41F 100 100 100 100 100 100 100 100 100 100                                                                               60  100                                                                               98 --                        42F 60  100 85  100 100 70  95  100 95  100                                                                               10  100                                                                               95 50                        43F 85  100 25  100 60  25  98  100 100 100                                                                               100 100                                                                               90 100                       44F 0   80  10  85  0   0   75  0   30  100                                                                               0   100                                                                               0  10                        45F 25  100 40  100 60  0   65  60  60  100                                                                               50  100                                                                               70 0                         50F --  100 50  100 35  35  75      100 100                                                                               --                                  __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE V-F                                    __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 0.56 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG  JG  WO BSG                                                                               AMG SESB                                                                               VL  SP MD YNS CB                           __________________________________________________________________________     46F 0  65 35  75  65  0  0  0   35  100 25 90 80  0                            47F -- 60 35  100 100 0  90 100 100 100 70 -- 100 75                           48F -- 75 20  90  60  0  15 70  35  90  0  -- 20  40                           49F -- 60 10  100 60  0  50 100 95  100 40 -- 90  100                          51F -- 40 10  95  40  10 50 65  100 100 0  -- 95  65                           __________________________________________________________________________      (--)  Not tested.                                                        

                                      TABLE VI-F                                   __________________________________________________________________________     Post-Emergence Multi-Weed Herbicidal Activity                                  Application Rate - 2.24 kg/ha                                                  Cmpd.                                                                          No. DB  FT  ARG WG  JG  WO  BSG AMG  SESB                                                                               VL   SP  MD   YNS                                                                               CB                   __________________________________________________________________________     19F 100 90  65  100 100 98  100 100  100 100  60  100  70 100                  26F 60  75  60  95  45  50  90  50   90  100  40  90   60 --                   27F 80  70  65  95  100 90  100 100  100 100  85  100  75 --                   28F 80  100 75  90  85  80  100 80   80  100  30  100  85 85                   29F 85  70  55  90  98  90  100 100  100 100  35  100  60 100                  30F 90  80  40  90  85  80  80  70   100 100  20  100  40 --                   31F 100 80  20  100 100 100 100 100  100 100  100 100  85 --                   32F 70  90  60  100 100 98  100 100  100 100  100 100  60 --                   33F 95  100 80  100 90  100 100 100  100 100  70  100  40 --                   35F 70  90  40  100 --  100 100 100  100 100  98  100  30 --                   36F 85  100 35  100 --  20  100 100  100 100  100 100  15 --                   39F 100 100 85  100 100 100 100 100  100 100  100 100  90 100                  40F 100 100 30  100 100 100 100 100  100 100  90  100  75 --                   41F 100 100 35  90  70  100 90  100  100 100  50  100  70 --                   42F 45  100 50  100 70  55  80  100  100 100  70  100  75 100                  43F 25  80  15  98  35  0   20  100  100 100  100 100  60 95                   44F 0   15  0   65  0   0   0   70   100 100  40  100  0  100                  45F 0   75  35  70  35  0   60  50   85  100  50  100  75 70                   50F --  40  0   75  45  40  60  100  100 95   30  --   60 100                  __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE VII-F                                  __________________________________________________________________________     Post-Emergence Multi-Weed Herbicidal Activity                                  Application Rate - 0.56 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG JG                                                                               WO BSG                                                                               AMG SESB                                                                               VL  SP                                                                               MD YNS                                                                               CB                                __________________________________________________________________________     46F 25 35 20  50 35                                                                               35 0  20  75  100 35                                                                               95 -- 50                                47F -- 75 25  90 40                                                                               25 80 100 100 100 80                                                                               -- 75 100                               48F -- 50 35  80 35                                                                               40 0  75  100 85  15                                                                               -- 50 75                                49F -- 35 0   75 30                                                                               0  20 100 100 100 80                                                                               -- 25 85                                51F -- 35 0   80 35                                                                               20 70 50  95  95  25                                                                               -- 65 50                                __________________________________________________________________________      (--) = Not Tested.                                                       

The compounds of the present invention and their salts are useful as herbicides and can be applied in a variety of ways at various concentrations. In practice, the compounds or salts are formulated into herbicidal compositions, by admixture, in herbicidally effective amounts, with the adjuvants and carriers normally employed for facilitating the dispersion of active ingredients for agricultural applications, recognizing the fact that the formulation and mode of application of a toxicant may affect the activity of the materials in a given application. Thus, these active herbicidal compounds or salts can be formulated as granules of relatively large particle size, as wettable powders, as emulsifiable concentrates, as powdery dusts, as flowables, as solutions or as any of several other known types of formulations, depending upon the desired mode of application. These formulations may contain as little as about 0.5% to as much as about 95% or more by weight of active ingredient. A herbicidally effective amount depends upon the nature of the seeds or plants to be controlled and the rate of application varies from about 0.01 to approximately 10 pounds per acre, preferably from about 0.02 to about 4 pounds per acre.

Wettable powders are in the form of finely divided particles which disperse readily water or other dispersants. The wettable powder is ultimately applied to the soil either as a dry dust or as a dispersion in water or other liquid. Typical carriers for wettable powders include fuller's earth, kaolin clays, silicas and other readily wet organic or inorganic diluents. Wettable powders normally are prepared to contain about 5% to about 95% of the active ingredient and usually also contain a small amount of wetting, dispersing, or emulsifying agent to facilitate wetting and dispersion.

Emulsifiable concentrates are homogeneous liquid compositions which are dispersible in water or other dispersant, and may consist entirely of the active compound or salt with a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromtic naphthal, isophorone and other non-volatile organic solvents. For herbicidal application, these concentrates are dispersed in water or other liquid carrier and normally applied as a spray to the area to be treated. The percentage by weight of the essential active ingredient may vary according to the manner in which the composition is to be applied, but in general comprises about 0.5% to 95% of active ingredient by weight of the herbicidal composition.

Granular formulations wherein the toxicant is carried on relatively coarse particles, are usually applied without dilution to the area in which suppression of vegetation is desired. Typical carriers for granular formulations include sand, fuller's earth, attapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite and other organic or inorganic materials which absorb or which may be coated with the toxicant. Granular formulations normally are prepared to contain about 0.1% to about 25% of active ingredients which may include surface-active agents such heavy aromatic naphthas, kerosene or other petroleum fractions, or vegetable oils; and/or stickers such as dextrins, glue or synthetic resins.

Typical wetting, dispersing or emulsifying agents and adjuvants used in agricultural formulations include, for example, the alkyl and alkylaryl sulfonates and sulfates and their salts; polyhydric alcohols; polyethoxylated alcohols, esters and fatty amines; and other types of surface-active agents, many of which are available in commerce. The surface-active agent, when used, normally comprises from 0.1% to 30% by weight of the herbicidal composition.

Dusts, which are free-flowing admixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids which act as dispersants and carriers for the toxicant, are useful formulations for soil-incorporating application.

Pastes, which are homogeneous suspensions of a finely divided solid toxicant in a liquid carrier such as water or oil, are employed for specific purposes. These formulations normally contain about 5% to about 95% of active ingredient by weight, and may also contain small amounts of a wetting, dispersing or emulsifying agent to facilitate dispersion. For application, the pastes are normally diluted and applied as a spray to the area to be affected.

Other useful formulations for herbicidal applications include simple solutions of the active ingredient in a dispersant in which it is completely soluble at the desired concentration, such as water, acetone, alkylated naphthalenes, xylene and other organic solvents. Pressurized sprays, typically aerosols, wherein the active ingredient is dispersed in finely-divided form as a result of vaporization of a low boiling dispersant solvent carrier, such as the Freons, may also be used.

The phytotoxic compositions of this invention can be applied to the plants in the conventional manner. Thus, the dust and liquid compositions can be applied to the plant by the use of power-dusters, boom and hand sprayers and spray dusters. The compositions can also be applied from airplanes as a dust or a spray or by rope wick applications because they are effective in very low dosages. In order to modify or control growth of germinating seeds or emerging seedlings, as a typical example, the dust and liquid compositions can be applied to the soil according to conventional methods and can be distributed in the soil to a depth of at least 1/2 inch below the soil surface. It is not necessary that the phytotoxic compositions be mechanically admixed with the soil particles since these compositions can also be applied merely by spraying or sprinkling the surface of the soil. The phytotoxic compositions of this invention can also be applied by addition to irrigation water supplied to the field to be treated. This method of application permits the penetration of the compositions into the soil as the water is absorbed therein. Dust compositions, granular compositions or liquid formulations applied to the surface of the soil can be distributed below the surface of the soil by conventional means such as discing, dragging or mixing operations. In the following examples the herbicidal compound can be substituted with the herbicidal salt of the compound.

    __________________________________________________________________________     General Formula with Ranges                                                                       Specific Formula                                            __________________________________________________________________________     EMULSIFIABLE CONCENTRATE FORMULATIONS                                          Herbicidal compound                                                                        5-55   herbicidal compound                                                                         24                                             surfactant(s)                                                                              5-25   proprietary blend of oil-                                                                   10                                             solvent(s)  20-90  soluble sulfonates and                                                  100%   polyoxyethylene ethers                                                         polar solvent                                                                               27                                                                petroleum hydrocarbon                                                                       39                                                                             100%                                           WETTABLE POWDER FORMULATIONS                                                   herbicidal compound                                                                        3-90   herbicidal compound                                                                         80                                             wetting agent                                                                              0.5-2  sodium dialkyl naphthalene                                                                  0.5                                            dispersing agent                                                                           1-8    sulfonate                                                   diluent(s)  8.5-87 sodium lignosulfonate                                                                       7                                                          100%   attapulgite clay                                                                            12.5                                                                           100%                                           EXTRUDED GRANULAR FORMULATIONS                                                 herbicidal compound                                                                        1-20   herbicidal compound                                                                         10                                             binding agent                                                                              0-10   lignin sulfonate                                                                            5                                              diluent(s)  70-99  calcium carbonate                                                                           85                                                         100%                100%                                           FLOWABLE FORMULATIONS                                                          herbicidal compound                                                                        20-70  herbicidal compound                                                                         45                                             surfactant(s)                                                                              1-10   polyoxyethylene ether                                                                       5                                              suspending agent(s)                                                                        0.05-1 attagel      0.05                                           antifreeze agent                                                                           1-10   propylene glycol                                                                            10                                             antimicrobial agent                                                                        1-10   1,2-benzisothiazoline-3-one                                                                 0.03                                           antifoam agent                                                                             0.1-1  silicone defoamer                                                                           0.02                                           solvent     7.95-77.85                                                                            water        39.9                                                       100%                100%                                           __________________________________________________________________________

When salts are used as the active ingredient in the herbicidal compositions of this invention it is recommended to use salts that are agriculturally acceptable.

The phytotoxic compositions of this invention can also contain other additives, for example, fertilizers, other herbicides and other pesticides, used as adjuvant or in combination with any of the above-described adjuvants. Fertilizers useful in combination with the active ingredients include, for example, ammonium nitrate, urea and superphosphate. 

We claim:
 1. Compounds of the formula ##STR96## wherein n is the integer 0, 1 or 2;R⁴⁰ is C₁ -C₄ alkyl; R⁴¹ is hydrogen or C₁ -C₄ alkyl; R⁴² is hydrogen, C₁ -C₄ alkyl or ##STR97## wherein R^(a) is C₁ -C₄ alkyl; or R⁴¹ and R⁴² together are alkylene having 3 to 6 carbon atoms; R⁴³ is hydrogen or C₁ -C₄ alkyl; R⁴⁴ is hydrogen or C₁ -C₄ alkyl; R⁴⁵ is hydrogen or C₁ -C₄ alkyl; R⁴⁶ is hydrogen or C₁ -C₄ alkyl; and R⁴⁷ and R⁴⁸ independently are (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl; (9) R^(b) SO_(n) 13 wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR^(r) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)--wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined, with the proviso that R⁴⁷ is not attached to the 6-position and their salts.
 2. The compound of claim 1 wherein n is 2; R⁴⁰ is methyl; R⁴¹ is hydrogen or methyl; R⁴² is hydrogen or methyl; R⁴³ is hydrogen or methyl; R⁴⁴ is hydrogen or methyl; R⁴⁵ is hydrogen or methyl; R⁴⁶ is hydrogen or methyl; R⁴⁷ and R⁴⁸ indepently are (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl; (9) R^(b) SO_(n) --wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)--wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined.
 3. The compound of claim 2 wherein R⁴⁷ and R⁴⁸ are independently are hydrogen; chlorine; fluorine; bromine; methyl; methoxy; trifluoromethoxy; cyano; nitro; trifluoromethyl; R^(b) SO_(n) --wherein n is the integer 2 and R^(b) is methyl, chloromethyl, trifluoromethyl, cyanomethyl, ethyl, or n-propyl; --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; R^(e) C(O)--where R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy or SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined and R⁴⁷ is in the 3-position.
 4. The compound of claim 2 wherein R⁴⁷ is hydrogen and R⁴⁸ is hydrogen, chlorine, bromine, fluorine, trifluoromethyl or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl.
 5. The compound of claim 1 wherein n is two; R⁴⁰ is methyl; R⁴¹ is methyl; R⁴² is methyl; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is hydrogen; R⁴⁶ is hydrogen; R⁴⁷ is hydrogen; and R⁴⁸ is hydrogen.
 6. The compound of claim 1 wherein n is two; R⁴⁰ is methyl; R⁴¹ is methyl; R⁴² is methyl; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is methyl; R⁴⁶ is hydrogen; R⁴⁷ is hydrogen; and R⁴⁸ is hydrogen.
 7. The compound of claim 1 wherein n is zero; R⁴⁰ is methyl; R⁴¹ is hydrogen; R⁴² is hydrogen; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is hydrogen; R⁴⁶ is hydrogen; R⁴⁷ is 3-chlorine; and R⁴⁸ is chlorine.
 8. The compound of claim 1 wherein n is two; R⁴⁰ is methyl; R⁴¹ is hydrogen; R⁴² is hydrogen; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is hydrogen; R⁴⁶ is hydrogen; R⁴⁷ is 3-chlorine; and R⁴⁸ is chlorine.
 9. The compound of claim 1 wherein n is zero; R⁴⁰ is methyl; R⁴¹ is hydrogen; R⁴² is hydrogen; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is hydrogen; R⁴⁶ is hydrogen; R⁴⁷ is hydrogen; and R⁴⁸ is trifluoromethyl.
 10. The compound of claim 1 wherein n is two; R⁴⁰ is methyl; R⁴¹ is hydrogen; R⁴² is hydrogen; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is hydrogen; R⁴⁶ is hydrogen; R⁴⁷ is hydrogen; and R⁴⁸ is trifluoromethyl.
 11. The compound of claim 1 wherein n is zero; R⁴⁰ is methyl; R⁴¹ is methyl; R⁴² is methyl; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is hydrogen; R⁴⁶ is hydrogen; R⁴⁷ is hydrogen; and R⁴⁸ is trifluoromethyl.
 12. The compound of claim 1 wherein n is two; R⁴⁰ is methyl; R⁴¹ is methyl; R⁴² is methyl; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is hydrogen; R⁴⁶ is hydrogen; R⁴⁷ is hydrogen; and R⁴⁸ is trifluoromethyl.
 13. The compound of claim 1 wherein n is one; R⁴⁰ is methyl; R⁴¹ is methyl; R⁴² is methyl; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is hydrogen; R⁴⁶ is hydrogen; R⁴⁷ is hydrogen; and R⁴⁸ is trifluoromethyl.
 14. The compound of claim 1 wherein n is zero; R⁴⁰ is methyl; R⁴¹ is hydrogen; R⁴² is hydrogen; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is hydrogen; R⁴⁶ is hydrogen; R⁴⁷ is 3-chlorine; and R⁴⁸ is methylthio.
 15. The compound of claim 1 wherein n is one; R⁴⁰ is methyl; R⁴¹ is hydrogen; R⁴² is hydrogen; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is hydrogen; R⁴⁶ is hydrogen; R⁴⁷ is 3-chlorine; and R⁴⁸ is CH₃ S(O)--.
 16. The method of controlling undesirable vegetation comprising applying to the area where control is desired, an herbicidally effective amount of a compound having the formula ##STR98## wherein n is the integer 0, 1 or 2;R⁴⁰ is C₁ -C₄ alkyl; R⁴¹ is hydrogen or C₁ -C₄ alkyl; R⁴² is hydrogen, C₁ -C₄ alkyl or ##STR99## wherein R^(a) is C₁ -C₄ alkyl; or R⁴¹ and R⁴² together are alkylene having 3 to 6 carbon atoms; R⁴³ is hydrogen or C₁ -C₄ alkyl; R⁴⁴ is hydrogen or C₁ -C₄ alkyl; R⁴⁵ is hydrogen or C₁ -C₄ alkyl; R⁴⁶ is hydrogen or C₁ -C₄ alkyl; and R⁴⁷ and R⁴⁸ independently are (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl; (9) R^(b) SO_(n) --wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)--whrein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined, with the proviso that R⁴⁷ is not attached to the 6-position or its salts.
 17. The method of claim 16 wherein n is 2; R⁴⁰ is is methyl; R⁴¹ is hydrogen or methyl; R⁴² is methyl; R⁴³ is hydrogen or methyl; R⁴⁴ is hydrogen or methyl; R⁴⁵ is hydrogen or methyl; R⁴⁶ is hydrogen or methyl; R⁴⁷ and R⁴⁸ independently are (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl; (9) R^(b) SO_(n) --wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)--wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined.
 18. The method of claim 17 wherein R⁴⁷ and R⁴⁸ are independently are hydrogen; chlorine; fluorine; bromine; methyl; methoxy; trifluoromethoxy; cyano; nitro; trifluoromethyl; R^(b) SO_(n) --wherein n is the integer 2 and R^(b) is methyl, chloromethyl, trifluoromethyl, cyanomethyl, ethyl, or n-propyl; --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; R^(e) C(O)--where R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy or SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined and R⁴⁷ is in the 3-position.
 19. The method of claim 16 wherein R⁴⁷ is hydrogen and R⁴⁸ is hydrogen, chlorine, bromine, fluorine, trifluoromethyl or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl.
 20. The method of claim 16 wherein n is two; R⁴⁰ is methyl; R⁴¹ is methyl; R⁴² is methyl; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is hydrogen; R⁴⁶ is hydrogen; R⁴⁷ is hydrogen; and R⁴⁸ is hydrogen.
 21. The method of claim 16 wherein n is two; R⁴⁰ is methyl; R⁴¹ is methyl; R⁴² is methyl; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is methyl; R⁴⁶ is hydrogen; R⁴⁷ is hydrogen; and R⁴⁸ is hydrogen.
 22. The method of claim 16 wherein n is zero; R⁴⁰ is methyl; R⁴¹ is hydrogen; R⁴² is hydrogen; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is hydrogen; R⁴⁶ is hydrogen; R⁴⁷ is 3-chlorine; and R⁴⁸ is chlorine.
 23. The method of claim 16 wherein n is two; R⁴⁰ is methyl; R⁴¹ is hydrogen; R⁴² is hydrogen; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is hydrogen; R⁴⁶ is hydrogen; R⁴⁷ is 3-chlorine; and R⁴⁸ is chlorine.
 24. The method of claim 16 wherein n is zero; R⁴⁰ is methyl; R⁴¹ is hydrogen; R⁴² is hydrogen; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is hydrogen; R⁴⁶ is hydrogen; R⁴⁷ is hydrogen; and R⁴⁸ is trifluoromethyl.
 25. The method of claim 16 wherein n is two; R⁴⁰ is methyl; R⁴¹ is hydrogen; R⁴² is hydrogen; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is hydrogen; R⁴⁶ is hydrogen; R⁴⁷ is hydrogen; and R⁴⁸ is trifluoromethyl.
 26. The method of claim 16 wherein n is zero; R⁴⁰ is methyl; R⁴¹ is methyl; R⁴² is methyl; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is hydrogen; R⁴⁶ is hydrogen; R⁴⁷ is hydrogen; and R⁴⁸ is trifluoromethyl.
 27. The method of claim 16 wherein n is two; R⁴⁰ is methyl; R⁴¹ is methyl; R⁴² is methyl; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is hydrogen; R⁴⁶ is hydrogen; R⁴⁷ is hydrogen; and R⁴⁸ is trifluoromethyl.
 28. The method of claim 16 wherein n is one; R⁴⁰ is methyl; R⁴¹ is methyl; R⁴² is methyl; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is hydrogen; R⁴⁶ is hydrogen; R⁴⁷ is hydrogen; and R⁴⁸ is trifluoromethyl.
 29. The method of claim 16 wherein n is zero; R⁴⁰ is methyl; R⁴¹ is hydrogen; R⁴² is hydrogen; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is hydrogen; R⁴⁶ is hydrogen; R⁴⁷ is 3-chlorine; and R⁴⁸ is methylthio.
 30. The method of claim 16 wherein n is one; R⁴⁰ is methyl; R⁴¹ is hydrogen; R⁴² is hydrogen; R⁴³ is hydrogen; R⁴⁴ is hydrogen; R⁴⁵ is hydrogen; R⁴⁶ is hydrogen; R⁴⁷ is 3-chlorine; and R⁴⁸ is CH₃ S(O)--.
 31. An heribicidal composition comprising an herbicidally active 2-(2-C₁ -C₄ alkylthio, C₁ -C₄ alkylsulfinyl or C₁ -C₄ alkylsulfonyl benzoyl)1,3-cyclhexanedione or its salts and an inert carrier therefor.
 32. The herbicidal composition of claim 31 wherein the 2-(2-C₁ -C₄ alkylthio, C₁ -C₄ alkylsulfinyl or C₁ -C₄ alkylsulfonyl benzoyl-1,3-cyclohexanedione is a compound of the formula ##STR100## wherein n is the integer 0, 1 or 2;R⁴⁰ is C₁ -C₄ alkyl; R⁴¹ is hydrogen or C₁ -C₄ alkyl; R⁴² is hydrogen, C₁ -C₄ alkyl or ##STR101## wherein R^(a) is C₁ -C₄ alkyl; or R⁴¹ and R⁴² together are alkylene having 3 to 6 carbon atoms; R⁴³ is hydrogen or C₁ -C₄ alkyl; R⁴⁴ is hydrogen or C₁ -C₄ alkyl; R⁴⁵ is hydrogen or C₁ -C₄ alkyl; R⁴⁶ is hydrogen or C₁ -C₄ alkyl; and R⁴⁷ and R⁴⁸ independently are (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl; (9) R^(b) SO_(n) --wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)--wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined, with the proviso that R⁴⁷ is not attached to the 6-position.
 33. The herbicidal composition of claim 32 wherein n is 2; R⁴⁰ is methyl; R⁴¹ is hydrogen or methyl; R⁴² is hydrogen or methyl; R⁴³ is hydrogen or methyl; R⁴⁴ is hydrogen or methyl; R⁴⁵ is hydrogen or methyl; R⁴⁶ is hydrogen or methyl; R⁴⁷ and R⁴⁸ independently are (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (=b 5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl; (9) R^(b) SO_(n) --wherein n is the integer 0, 1 to 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)--wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined.
 34. The herbicidal composition of claim 33 wherein R⁴⁷ and R⁴⁸ are independently are hydrogen; chlorine; fluorine; bromine; methyl; methoxy; trifluoromethoxy; cyano; nitro; trifluoromethyl; R^(b) SO_(n) --wherein n is the integer 2 and R^(b) is methyl, chloromethyl, trifluoromethyl, cyanomethyl, ethyl, or n-propyl; --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; R^(e) C(O)--where R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy or SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined and R⁴⁷ is in the 3-position. 